Language：English   Publishing type：Research paper (scientific journal)  

An efficient approach to a variety of chiral silacyclopentanes having silicon stereogenic center based on the stereospecific transformations of C4 carbon stereogenic center of silacyclopentenols by Mitsunobu reaction or Tsuji-Trost reaction has been developed. The thus obtained substitution products can be converted into novel silacyclopentane triols, amines, and carboxylic acids in stereospecific manner.

DOI： 10.1055/s-0036-1590826

Language：English   Publishing type：Research paper (scientific journal)  

Newly designed buckle units for copper-free click chemistry: 4,8-diazacyclononynes (DACNs) were efficiently synthesized with a one-pot procedure from commercially available 2-butyne-1,4-diol. The synthesized DACNs possess versatile connectors for the introduction of functional units and exhibit high click reactivity.

DOI： 10.1055/s-0036-1588839

Language：English   Publishing type：Research paper (scientific journal)  

Nine-membered E,Z-diallylic heterocycles 1 and [7]-orthocyclphenes 2 exhibit planar chirality at ambient temperature. Their stereochemical stabilities are highly dependent on substituent R1 on the E-Alkene, embedded heteroatom X in the ring, and ring size. Their planar chirality can be transformed into carbon central chirality without loss of enantiopurity. Therefore, they are useful chiral building blocks for biologically active chiral molecules and precursors for chiral reagents. The enantioenriched forms of 1 and 2 are available by optical resolution of racemate, and asymmetric synthesis based on enantioselective cyclization. Planar chiral dialkoxysilane 32 and ketone 33 were also developed.

DOI： 10.5059/yukigoseikyokaishi.75.449

Language：English   Publishing type：Research paper (scientific journal)  

An efficient synthesis of (E)-4-[7]orthocyclophene (E)-1 via photochemical isomerization of (Z)-1 has been achieved. The key intermediate (Z)-1 was synthesized from commercially available 2-(hydroxymethyl)benzenepropanol (3) in five steps: (i) group-selective Mitsunobu reaction with CH₂=CHCH₂CH(SO₂Ph)₂, (ii) oxidation of alcohol, (III) olefination, (iv) RCM, and (v) removal of sulfones in an overall yield of 73%. The photochemical isomerization of (Z)-1 was efficiently performed in the presence of AgNO₃-impregnated silica gel (AgNO₃/SiO₂). The resulting (E)-1 shows dynamic planar chirality at rt. Enantioenriched (E)-1 was prepared by the HPLC separation of enantiomers using a chiral stationary phase, and the absolute stereochemistry was determined by X-ray diffraction analysis of the Pt-coordinated crystalline derivative. The planar chirality of (E)-1 can be converted into the central chirality of carbon; e.g., the oxidation of (R)-(E)-1 using DMDO provided epoxide (8S,9S)-9 in a stereospecific manner. Furthermore, the Lewis acid-promoted reaction of (8S,9S)-9 afforded a unique tricyclic compound (8S,9S)-10 in an excellent yield and in a stereospecific manner.

DOI： 10.1021/acs.joc.6b01799

Language：English   Publishing type：Research paper (scientific journal)  

A variety of functionalized silacyclopentanes were synthesized by highly enantioselective β‐eliminations of silacyclopentene oxides followed by stereospecific transformations. The reaction mechanism of the β‐elimination was elucidated by DFT calculations. An in vitro biological assay with an oxy‐functionalized silacyclopentane showed substantial binding to a serotonin receptor protein.

DOI： DOI: 10.1002/anie.201511728

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DOI： 10.1021/jacs.5b04340

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DOI： 10.1002/chem.201402434

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DOI： 10.1246/cl.130735

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DOI： 10.1021/ja309642r

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DOI： 10.1002/anie.201207361

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DOI： 10.1002/anie.201204484

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アルキンの変換法として重要なヒドロシリル化反応について，従来は困難であった「反応の位置制御」の問題を解決した．具体的には，分子内に配向基を導入することでヒドロシリル化反応を触媒する白金錯体の位置を制御し，その結果としての生成物の位置制御を行うという新手法を開発した．本法により，精密有機合成化学において重要な非対称アルケニルシランの効率的合成が初めて可能となった．

DOI： 10.1021/ja209553f

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DOI： 10.1021/ol202009x

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DOI： 10.1246/cl.2011.591

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DOI： 10.1246/cl.2011.233

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DOI： 10.1021/ja1092375

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Language：English   Publisher：Organic Letters  

A catalyst-free triazole formation reaction between o-borylaryl azides and N-propargyldiethanolamine derivatives is reported. Control experiments demonstrated that the triazole formation was triggered by boronate formation, which brought the azido group and alkyne moiety into close proximity. This boronate formation-triggered azide-alkyne cycloaddition (BAAC) reaction exhibited orthogonality to other azide-alkyne cycloaddition reactions, enabling sequential double-click conjugations with diazido or dialkyne compounds.

DOI： 10.1021/acs.orglett.5c00732

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Language：English   Publisher：Chemistry - A European Journal  

4,4′-Biazulene is a potentially attractive key component of an axially chiral biaryl compound, however, its structure and properties have not been clarified owing to the lack of its efficient synthesis. We report a breakthrough in the reliable synthesis of 4,4′-biazulene, which is achieved by the access to azulen-4-ylboronic acid pinacol ester and 4-iodoazulene as novel key synthetic intermediates for the Suzuki-Miyaura cross-coupling reaction. The X-ray crystallographic analysis of 4,4′-biazulene confirmed its axial chirality. The enantiomers of 4,4′-biazulene were successfully resolved by HPLC on the chiral stationary phase column. The kinetic experiments and DFT calculations indicate that the racemization energy barrier of 4,4′-biazulene is comparable to that of 1,1′-binaphthyl.

DOI： 10.1002/chem.202400098

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PubMed

Language：Japanese   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：Japanese   Publishing type：Research paper (scientific journal)  

Publisher：Chemistry Letters  

We have synthesized multifunctionalized silacyclopentanes in a highly selective manner from enantioenriched silacyclopentenol, which is readily accessible from achiral silacyclopentene oxide by enantioselective β-elimination. Functionalization at C2, C4, and C5 positions of silacyclopentenol was achieved based on the regio- and stereoselective nucleophilic substitution reaction of epoxides.

DOI： 10.1093/chemle/upae039

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Language：English   Publisher：Journal of the American Chemical Society  

The acetal (O-glycoside) bonds of glycans and glycoconjugates are chemically and biologically vulnerable, and therefore C-glycosides are of interest as more stable analogs. We hypothesized that, if the O-glycoside linkage plays a vital role in glycan function, the biological activities of C-glycoside analogs would vary depending on their substituents. Based on this idea, we adopted a “linkage-editing strategy” for the creation of glycan analogs (pseudo-glycans). We designed three types of pseudo-glycans with CH2 and CHF linkages, which resemble the O-glycoside linkage in terms of bond lengths, angles, and bulkiness, and synthesized them efficiently by means of fluorovinyl C-glycosylation and selective hydrogenation reactions. Application of this strategy to isomaltose (IM), an inducer of amylase expression, and α-GalCer, which activates iNKT cells, resulted in the discovery of CH2-IM, which shows increased amylase production ability, and CHF-α-GalCer, which shows activity opposite that of native α-GalCer, serving as an antagonist of iNKT cells.

DOI： 10.1021/jacs.3c12581

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CiNii Research

Language：English   Publisher：Life Sciences  

Aims: Differentiation-inducing factor-1 (DIF-1), a compound in Dictyostelium discoideum, exhibits anti-cancer effects by inhibiting cell proliferation and motility of various mammalian cancer cells in vitro and in vivo. In addition, DIF-1 suppresses lung colony formation in a mouse model, thus impeding cancer metastasis. However, the precise mechanism underlying its anti-metastatic effect remains unclear. In the present study, we aim to elucidate this mechanism by investigating the adhesion of circulating tumor cells to blood vessels using in vitro and in vivo systems. Main methods: Melanoma cells (1.0 × 105 cells) were injected into the tail vein of 8-week-old male C57BL/6 mice after administration of DIF-1 (300 mg/kg per day) and/or lipopolysaccharide (LPS: 2.5 mg/kg per day). To investigate cell adhesion and molecular mechanisms, cell adhesion assay, western blotting, immunofluorescence staining, and flow cytometry were performed. Key findings: Intragastric administration of DIF-1 suppressed lung colony formation. DIF-1 also substantially inhibited the adhesion of cancer cells to human umbilical vein endothelial cells. Notably, DIF-1 did not affect the expression level of adhesion-related proteins in cancer cells, but it did decrease the expression of vascular cell adhesion molecule-1 (VCAM-1) in human umbilical vein endothelial cells by suppressing its mRNA-to-protein translation through inhibition of mTORC1-p70 S6 kinase signaling. Significance: DIF-1 reduced tumor cell adhesion to blood vessels by inhibiting mTORC1-S6K signaling and decreasing the expression of adhesion molecule VCAM-1 on vascular endothelial cells. These findings highlight the potential of DIF-1 as a promising compound for the development of anti-cancer drugs with anti-metastatic properties.

DOI： 10.1016/j.lfs.2023.122278

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Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：Chemistry - A European Journal  

Small chiral organic molecules with CD properties are in high demanded due to their potential use in promising electronic and biological applications. Herein, we reveal a system in which the oxidation of a phosphino group to the corresponding phosphine oxide on the inner rim of a helicene derivative induces a CPL response. Laterally π-extended 7,8-dihydro[5]helicenes bearing phosphine and phosphine oxide groups on their inner helical rims (i. e., the C1 position) were synthesized, and their helical structures were unambiguously determined by X-ray crystallography. The photophysical (UV/visible and emission) and chiroptical properties of these compounds were investigated in various solvents. Despite their structural similarities, phosphine oxide showed a significantly better CPL response than phosphine, with a high dissymmetry factor for emission (|glum|=(1.3–1.9)×10−3) that can be attributed to structural changes in the interior of the helicene helix.

DOI： 10.1002/chem.202202922

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Language：English   Publisher：Chemical Communications  

DACN-NHS-ester and DACN-maleimide were developed as molecular connectors and applied for the synthesis of artificial hybrid biomolecules in two steps, including, step 1: connection to a corresponding molecule via the NHS ester or maleimide unit, followed by step 2: connection to a corresponding azido-containing molecule via DACN unit by copper-free-alkyne-azide-cycloaddition.

DOI： 10.1039/d3cc03023g

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Language：English   Publishing type：Research paper (scientific journal)  

Language：Japanese   Publishing type：Research paper (scientific journal)  

DOI： 1246/cl.220219

Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：Chirality  

The presence of planar chirality of a variety of medium-sized heterocycles, along with nine-membered cyclic ketone and its enol ester, was revealed by observation of isolable enantiomers by analytical high-performance liquid chromatography (HPLC) using a chiral stationary phase with a polysaccharide-based chiral selector. Several tens of milligrams of enantiomers of the planar-chiral molecules were successfully separated by preparative-scale HPLC, leading to the preparation of an enantioenriched sample. This in turn enabled detailed stereochemical studies, including measurement of half-lives of the optical activity and X-ray crystallography for elucidation of stereochemistry.

DOI： 10.1002/chir.23429

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Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：Journal of Pharmacological Sciences  

Differentiation-inducing factor 1 (DIF-1) is a morphogen produced by Dictyostelium discoideum that inhibits the proliferation and migration of both D. discoideum and most mammalian cells. Herein, we assessed the effect of DIF-1 on mitochondria, because DIF-3, which is similar to DIF-1, reportedly localizes in the mitochondria when added exogenously, however the significance of this localization remains unclear. Cofilin is an actin depolymerization factor that is activated by dephosphorylation at Ser-3. By regulating the actin cytoskeleton, cofilin induces mitochondrial fission, the first step in mitophagy. Here, we report that DIF-1 activates cofilin and induces mitochondrial fission and mitophagy mainly using human umbilical vein endothelial cells (HUVECs). AMP-activated kinase (AMPK), a downstream molecule of DIF-1 signaling, is required for cofilin activation. Pyridoxal phosphatase (PDXP)—known to directly dephosphorylate cofilin—is also required for the effect of DIF-1 on cofilin, indicating that DIF-1 activates cofilin through AMPK and PDXP. Cofilin knockdown inhibits mitochondrial fission and decreases mitofusin 2 (Mfn2) protein levels, a hallmark of mitophagy. Taken together, these results indicate that cofilin is required for DIF-1- induced mitochondrial fission and mitophagy.

DOI： 10.1016/j.jphs.2023.02.009

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Language：English   Publisher：(公社)日本薬理学会  

分化誘導因子1(DIF-1)がミトコンドリア(MT)の分裂に及ぼす影響について検討し、その分子メカニズムを調べた。ヒト臍帯静脈内皮細胞にて、DIF-1はマイトファジーの第1段階を誘導するコフィリン(COF)を活性化した。またDIF-1シグナル伝達によるCOF活性化にはAMP活性化キナーゼ(AMPK)が必要であり、COFを直接脱リン酸化するピリドキサールリン酸(PDXP)も必要であったため、DIF-1はAMPKとPDXPを介してCOFを活性化することが示された。COFノックダウンはMTの分裂を阻害し、マイトファジーの特徴であるMfn2蛋白質レベルを低下させた。

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publisher：International Immunopharmacology  

The tumor microenvironment (TME), largely composed of tumor-associated macrophages (TAMs) and cancer-associated fibroblasts (CAFs), plays a key role in cancer progression. A small molecule, differentiation-inducing factor-1 (DIF-1) secreted by Dictyostelium discoideum, is known to exhibit anticancer activity; however, its effect on the TME remains unknown. In this study, we investigated the effect of DIF-1 on the TME using mouse triple-negative breast cancer 4T1-GFP cells, mouse macrophage RAW 264.7 cells, and mouse primary dermal fibroblasts (DFBs). Polarization of 4T1 cell-conditioned medium-induced macrophage into TAMs was not affected by DIF-1. In contrast, DIF-1 decreased 4T1 cell co-culturing-induced C-X-C motif chemokine ligand 1 (CXCL1), CXCL5, and CXCL7 expression in DFBs and suppressed DFB differentiation into CAF-like cells. Additionally, DIF-1 inhibited C-X-C motif chemokine receptor 2 (CXCR2) expression in 4T1 cells. Immunohistochemical analyses of tumor tissue samples excised from breast cancer-bearing mice showed that DIF-1 did not affect the number of CD206-positive TAMs; however, it decreased the number of α-smooth muscle actin-positive CAFs and CXCR2 expression. These results indicated that the anticancer effect of DIF-1 was partially attributed to the inhibition of CXCLs/CXCR2 axis-mediated communication between breast cancer cells and CAFs.

DOI： 10.1016/j.intimp.2023.109913

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Language：English   Publisher：Chemistry (Weinheim an der Bergstrasse, Germany)  

Invited for the cover of this issue are the groups of Kazuteru Usui and Satoru Karasawa at Showa Pharmaceutical University, and Yoshitane Imai at Kindai University. The image depicts how a phosphine-oxide-bearing helicene exhibits markedly enhanced CPL response in the excited state compared with that of one with a corresponding phosphine. Read the full text of the article at 10.1002/chem.202202922.

DOI： 10.1002/chem.202203413

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Language：Japanese   Publisher：The Society of Synthetic Organic Chemistry, Japan  

DOI： 10.5059/yukigoseikyokaishi.80.872

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CiNii Research

Language：Japanese   Publishing type：Research paper (scientific journal)  

Publisher：Chemistry Letters  

Planar chiral oxa-[7]orthocyclophene 1a was designed and synthesized with two different synthetic routes. X-ray crystallographic analyses of 1a and its platinum complex revealed a highly distorted ring structure and the absolute stereochemistry of 1a, respectively. Epoxidation and [2,3]-Wittig rearrangement of 1a provided with central chiral molecules, without the loss of enantiomeric purity.

DOI： 10.1246/cl.220219

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Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：Chemistry Letters  

Newly synthesized ten-membered diallylic nitrogen cycle, having E- and Z-alkene moieties, shows labile planar-chirality at ambient temperature. VT-NMR experiments revealed the detail of the stereochemical behavior of interconversion of the enantiomers and diastereomers. In sharp contrast, Pt-complex of the nitrogen cycle have more stable planar chirality, and the enantiomers of the Pt-complex were isolated by HPLC using a chiral stationary phase.

DOI： 10.1246/cl.220143

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Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：Heterocycles  

Aza-orthocyclophyne 3b with an oxy-substituent on the 16 position of the benzene ring was synthesized, and it was revealed that the stereochemical stability of 3b is consistent with the order of 1,3-steric repulsion between the C2 methylene protons and the oxy-substituent.

DOI： 10.3987/COM-22-S(R)18

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Biochemical Pharmacology  

We previously reported that 2,5-dimethylcelecoxib (DM-C), a derivative of celecoxib, lacks cyclooxygenase-2 inhibitory effects and suppresses cardiac remodeling by activating glycogen synthase kinase-3 (GSK-3). However, it remains unclear whether DM-C attenuates fibroblast-to-myofibroblast transformation (FMT), which plays a key role in cardiac fibrosis. Therefore, we evaluated the effect of DM-C on FMT using a cryoinjury-induced myocardial infarction (CMI) mouse model. We found that DM-C attenuated the deterioration of left ventricular ejection fraction after CMI by decreasing cardiac fibrosis. Analysis of the expression level of α-smooth muscle actin (α-SMA), a marker for myofibroblasts, indicated that DM-C decreased FMT at the cardiac injury site. To investigate the mechanism by which DM-C attenuated FMT, fibroblasts obtained from the heart were stimulated with TGF-β to induce FMT, and the effect of DM-C was analyzed. DM-C suppressed the expression of α-SMA and the phosphorylation levels of Smad 2/3 and GSK-3, indicating that DM-C suppressed α-SMA expression by inhibiting the transforming growth factor (TGF)-β signaling pathway via activation of GSK-3. DM-C decreased the expression of collagen, connective tissue growth factor (CTGF) and Snail, which are also known to accelerate cardiac fibrosis. These results suggested that DM-C attenuated cardiac fibrosis by suppressing FMT at the injured site after CMI by inhibiting the TGF-β signaling pathway via activation of GSK-3. Thus, DM-C has potential against cardiac disease as a novel anti-fibrotic agent.

DOI： 10.1016/j.bcp.2022.114950

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Chemistry Letters  

The generation of 3-azidoarynes from o-iodoaryl triflatetype precursors was achieved using a silylmethyl Grignard reagent as the activator. The azido group served to control the regioselectivity of the reaction of 3-azidoarynes with arynophiles. The remaining azido group in the adduct also served as a transformable functional group, enabling further derivatization to various nitrogen-containing compounds.

DOI： 10.1246/cl.210632

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Molecules  

Seven mono-and dihydroxycholesterols were prepared by direct C–H oxidation of the cholestane skeleton with a recently developed Ru(Bpga) catalyst (Ru(Bpga) = [RuCl (bpga) (PPh3 )] Cl; bpga = 2-(bis(pyridin-2-ylmethyl)amino)-N-(2,6-dimethylphenyl)acetamide)). Due to the high selectivity of the Ru(Bpga) complex for tertiary C–H, the reaction afforded a mixture of 25-, 20-, 17-, and 14-oxygenated cholesterols that could be easily separated by high-performance liquid chromatography. These results suggest that late-stage C–H oxidation could be a viable strategy for preparing candidate metabolites of biologically important molecules.

DOI： 10.3390/molecules27010225

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1038/s41388-021-01958-4

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/chir.23264

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DOI： 10.1039/D0CC05182A

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/D0CC04606J

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/D0DT01223H

Language：English   Publishing type：Research paper (scientific journal)  

The addition-type ozone oxidation of silylalkenes is a highly efficient reaction to provide synthetically versatile α-silylperoxy carbonyl compounds. To gain insight into the reaction mechanism, we performed a computational study, which revealed that the reaction proceeds via [1,2]-Brook rearrangement-type silyl migration of primary ozonide. In sharp contrast to the addition-type reactions, the ozone oxidation of α-alkoxysilylalkenes proceeds in a cleavage-type manner to afford excellent yields of silacarboxylic acid esters via the 1,3-cycloelimination of primary ozonide prior to 1,2-silyl migration.

DOI： 10.1021/acs.joc.9b03350

Language：English   Publishing type：Research paper (scientific journal)  

Mid-sized molecules have emerged as an attractive chemical space and potentially provide a robust basis for the development of synthetic agents to control intracellular protein interactions. However, the limited cell permeability and chemical tractability of such agents remain to be addressed. We envisioned that target-templated synthesis of such mid-sized molecules might provide a solution. Here, we exploited a copper-free Huisgen cycloaddition for template synthesis using a peptide fragment containing a 4,8-diazacyclononyne (DACN) moiety and an azide-containing fusicoccin derivative in the presence or absence of recombinant 14-3-3ζ protein in vitro. Time-course changes in the yield of products demonstrated that the reaction was accelerated in the presence of 14-3-3 and one of the regioisomers was generated predominantly, supporting the template effect.

DOI： 10.1002/asia.202000042

Language：English   Publishing type：Research paper (scientific journal)  

Differentiation-inducing factor-1 (DIF-1) has been reported to inhibit the proliferation of various mammalian cells by unknown means, although some possible mechanisms of its action have been proposed, including the activation of glycogen synthase kinase-3 (GSK-3). Here, we report an alternative mechanism underlying the action of DIF-1 in human breast cancer cell line MCF-7, on which the effects of DIF-1 have not been examined previously. Intragastric administration of DIF-1 reduced the tumor growth from MCF-7 cells injected into a mammary fat pad of nude mice, without causing adverse effects. In cultured MCF-7, DIF-1 arrested the cell cycle in G₀/G₁ phase and suppressed cyclin D1 expression, consistent with our previous results obtained in other cell species. However, DIF-1 did not inhibit the phosphorylation of GSK-3. Investigating an alternative mechanism for the reduction of cyclin D1, we found that DIF-1 reduced the protein levels of signal transducer and activator of transcription 3 (STAT3). The STAT3 inhibitor S3I-201 suppressed cyclin D1 expression and cell proliferation and the overexpression of STAT3 enhanced cyclin D1 expression and accelerated proliferation. Differentiation-inducing factor-1 did not reduce STAT3 mRNA or reduce STAT3 protein in the presence of cycloheximide, suggesting that DIF-1 inhibited STAT3 protein synthesis. Seeking its mechanism, we revealed that DIF-1 inhibited the activation of 70 kDa and/or 85 kDa ribosomal protein S6 kinase (p70^S6K/p85^S6K). Inhibition of p70^S6K/p85^S6K by rapamycin also reduced the expressions of STAT3 and cyclin D1. Therefore, DIF-1 suppresses MCF-7 proliferation by inhibiting p70^S6K/p85^S6K activity and STAT3 protein synthesis followed by reduction of cyclin D1 expression.

DOI： 10.1111/cas.14204

Language：English   Publishing type：Research paper (scientific journal)  

We previously reported that 2,5-dimethylcelecoxib (DM-celecoxib), a celecoxib derivative that is unable to inhibit cyclooxygenase-2, prevented cardiac remodeling by activating glycogen synthase kinase-3 (GSK-3) and prolonged the lifespan of heart failure mice with genetic dilated cardiomyopathy or transverse aortic constriction-induced left ventricular hypertrophy. However, it remained unclear how DM-celecoxib regulated structure and function of cardiomyocytes and cardiac fibroblasts involved in cardiac remodeling. In the present study, therefore, we investigated the effect of DM-celecoxib on isoprenaline-induced cardiomyocyte hypertrophy and cardiac fibroblast activation, because DM-celecoxib prevented isoprenaline-induced cardiac remodeling in vivo. DM-celecoxib suppressed isoprenaline-induced neonatal rat cardiomyocyte hypertrophy by the inhibition of Akt phosphorylation resulting in the activation of GSK-3 and the inhibition of β-catenin and mammalian target of rapamycin (mTOR). DM-celecoxib also suppressed the proliferation and the production of matrix metalloproteinase-2 and fibronectin of rat cardiac fibroblasts. Moreover, we found that phosphatase and tensin homolog on chromosome 10 (PTEN) could be a molecule to mediate the effect of DM-celecoxib on Akt. These results suggest that DM-celecoxib directly improves the structure and function of cardiomyocytes and cardiac fibroblasts and that this compound could be clinically useful for the treatment of β-adrenergic receptor-mediated maladaptive cardiac remodeling.

DOI： 10.1016/j.bcp.2019.06.018

Language：English   Publishing type：Research paper (scientific journal)  

Development of supramolecular methods to further activate a highly reactive intermediate is a fascinating strategy to create novel potent catalysts for activation of inert chemicals. Herein, a supramolecular approach to enhance the oxidizing ability of a high-valent oxo species of a nitrido-bridged iron porphyrinoid dimer that is a known potent molecular catalyst for light alkane oxidation is reported. For this purpose, a nitrido-bridged dinuclear iron complex of porphyrin-phthalocyanine heterodimer 3
⁵⁺
, which is connected through a fourfold rotaxane, was prepared. Heterodimer 3
⁵⁺
catalyzed ethane oxidation in the presence of H
₂
O
₂
at a relatively low temperature. The site-selective complexation of 3
⁵⁺
with an additional anionic porphyrin (TPPS
⁴⁻
) through π–π stacking and electrostatic interactions afforded a stable 1:1 complex. It was demonstrated that the supramolecular post-synthetic modification of 3
⁵⁺
enhances its catalytic activity efficiently. Moreover, supramolecular conjugates achieved higher catalytic ethane oxidation activity than nitrido-bridged iron phthalocyanine dimer, which is the most potent iron-oxo-based molecular catalyst for light-alkane oxidation reported so far. Electrochemical measurements proved that the electronic perturbation from TPPS
⁴⁻
to 3
⁵⁺
enhanced the catalytic activity.

DOI： 10.1002/chem.201805580

Language：English   Publishing type：Research paper (scientific journal)  

Catalytic methane oxidation was conducted using a μ-nitrido-bridged dinuclear iron complex of a four-fold rotaxane heterodimer of a porphyrin and a phthalocyanine. Extension of the π-stacked structure of the four-fold rotaxane-based μ-nitrido-bridged iron porphyrinoid dimer by supramolecular complexation with an additional tetraanionic porphyrin apparently increased the methane conversion ability.

DOI： 10.1039/c9nj02210d

Language：English   Publishing type：Research paper (scientific journal)  

π-Conjugated helicenes containing heteroatoms have attracted significant attention due to their diverse chemical and electronic structures, as well as tunable physical properties. It was rationally anticipated that the self-assembly of coumarin-fused helicenes would be controlled by the effects of a substituent on the internal edge of the helix. Here, this work reports the efficient syntheses of coumarin-fused helicenes 1 a,b (R=Ph, Me), and the enantioselective synthesis of 1 a (R=Ph) by chiral Au^I-catalyzed hydroarylation. The helical structure of 1 was unambiguously determined by X-ray crystallography. Of particular note, the enantiomerically pure crystal of 1 a adopted a one-dimensional columnar structure based on π–π stacking interactions, as expected. Furthermore, a significant difference between the fluorescence quantum yields of the enantiomerically pure form and racemate of 1 a was observed.

DOI： 10.1002/chem.201803270

Language：English   Publishing type：Research paper (scientific journal)  

A new synthetic approach to novel axially chiral benzocarbazole derivatives based on the highly enantioselective intramolecular hydroarylation (94-96% ee) of linked alkyne-indole systems by using the prevalent chiral base catalyst, cinchonidine or cinchonine, under unprecedented transition-metal-free conditions is described. The process is considered to involve chiral base catalysis for enantioselective transformation of the alkyne part to a reaction intermediate with an axially chiral vinylidene o-quinone methide (VQM) functionality, which subsequently effects stereospecific cyclization with the tethered indole moiety.

DOI： 10.1021/acs.orglett.8b01945

Language：English   Publishing type：Research paper (scientific journal)  

A method for protecting organic azides from click reactions with alkynes is reported. Treatment of azides with Amphos affords phosphazides, which are stable under click reaction conditions and are easily converted back to azides by treatment with elemental sulfur. Thus, the method allows for facile modification of azide compounds via site-selective click reactions.

DOI： 10.1021/acs.orglett.8b01692

Language：English   Publishing type：Research paper (scientific journal)  

Vinylidene ortho-quinone methides (VQMs) are one-carbon elongated homologues of ortho-quinone methides (QMs), well-known as useful reaction intermediates in organic transformations. These related quinone methides are quite distinct in terms of stereochemistry. Namely, VQMs are characterized by an exocyclic allenyl ketone unit merged with a dearomatized ring system and thus, can be rendered axially chiral by locating a substituent properly at the terminal methylene group of the allene moiety. It should be also noted that VQMs are tautomers of ortho-ethynylphenols and these isomeric species are correlated through a proton-shift (tautomerization). Focusing on these stereochemical and structural features, we have pursued the development of unprecedented asymmetric reactions involving enantioenriched VQM intermediates generated by chiral-basecatalyzed tautomerization of the ethynylphenol precursors. Indeed, commonly used chiral base catalysts such as cinchonine (CN) and cinchonidine (CD) have been successfully demonstrated to be effective to this end. In this account, we wish to briefly describe our recent studies on the asymmetric syntheses of optically active indeno[1,2-c]chromenes, benzofuro[3,2-b]indeno[1,2-c]chromenes, and benzo[a]carbazoles, based on the catalytic enantioselective generation of VQMs with CN or CD and the stereocontrolled intramolecular follow-up cyclization with tethered alkynes, benzofurans, and indoles, respectively.

DOI： 10.2533/chimia.2018.892

Language：English   Publishing type：Research paper (scientific journal)  

A base-catalyzed stereoselective intramolecular dearomatizative [4+2] cycloaddition of o-phenylene-linked ethynylnaphthol–benzofuran systems was explored. In this reaction, we presume the involvement of electrophilic vinylidene o-quinone methides (4π), which add across the electron-rich furan double bonds (2π) to produce elaborate, fused oxa-polyheterocyclic frameworks with consecutive quaternary and tertiary asymmetric carbon atoms as single diastereomers. The catalytic and enantioselective synthesis of these chiral fused polyheterocyclic structures is also feasible with the use of a prevalent cinchonidine or cinchonine chiral base.

DOI： 10.1002/ejoc.201701481

Language：English   Publishing type：Research paper (scientific journal)  

Facile synthetic methods for condensed polycyclic aromatic compounds via aryne intermediates are reported. The generation of arynes bearing a (3-arylpropargyl)oxy group from the corresponding o-iodoaryl triflate-type precursors efficiently afforded arene-fused oxaacenaphthene derivatives, which were formed through intramolecular [2+4] cycloaddition. Extending the method to the generation of arynes bearing a 1,3-diyne moiety led to a continuous generation of naphthalyne intermediate through the hexadehydro Diels–Alder reaction involving the aryne triple bond. This novel type of aryne-relay chemistry enabled the synthesis of a unique aminoarylated oxaacenaphthene derivative and highly ring-fused anthracene derivatives.

DOI： 10.1002/chem.201704345

Language：English   Publishing type：Research paper (scientific journal)  

Differentiation-inducing factor-1 (DIF-1) isolated from Dictyostelium discoideum strongly inhibits the proliferation of various mammalian cells through the activation of glycogen synthase kinase-3 (GSK-3). To evaluate DIF-1 as a novel anti-cancer agent for malignant melanoma, we examined whether DIF-1 has anti-proliferative, anti-migratory, and anti-invasive effects on melanoma cells using in vitro and in vivo systems. DIF-1 reduced the expression levels of cyclin D1 and c-Myc by facilitating their degradation via GSK-3 in mouse (B16BL6) and human (A2058) malignant melanoma cells, and thereby strongly inhibited their proliferation. DIF-1 suppressed the canonical Wnt signaling pathway by lowering the expression levels of transcription factor 7-like 2 and β-catenin, key transcription factors in this pathway. DIF-1 also inhibited cell migration and invasion, reducing the expression of matrix metalloproteinase-2; however, this effect was not dependent on GSK-3 activity. In a mouse lung tumor formation model, repeated oral administrations of DIF-1 markedly reduced melanoma colony formation in the lung. These results suggest that DIF-1 inhibits cell proliferation by a GSK-3-dependent mechanism and suppresses cell migration and invasion by a GSK-3-independent mechanism. Therefore, DIF-1 may have a potential as a novel anti-cancer agent for the treatment of malignant melanoma.

DOI： 10.1016/j.bcp.2017.05.004

Language：English   Publishing type：Research paper (scientific journal)  

Glycogen synthase kinase-3 (GSK-3) is a crucial regulator of cardiac hypertrophy. We previously reported that 2,5-dimethylcelecoxib (DM-celecoxib), a celecoxib derivative unable to inhibit cyclooxygenase-2, prevented cardiac remodeling by activating GSK-3, resulting in lifespan prolongation in a mouse model of genetic dilated cardiomyopathy. In the present study, we investigated whether DM-celecoxib can also prevent pressure-induced cardiac remodeling and heart failure, elicited by transverse aortic constriction (TAC). Before testing the effects of DM-celecoxib, we compared the effects of TAC on the hearts of wild-type and GSK-3β hetero-deficient (GSK-3β^+/-) mice to determine the role of GSK-3 in cardiac remodeling and heart failure. GSK-3β^+/- mouse hearts exhibited more severe hypertrophy, which was characterized by accelerated interstitial fibrosis, than wild-type mouse hearts after TAC, suggesting that reduced GSK-3β activity aggravates pressure-induced left ventricular remodeling. We subsequently examined the effects of DM-celecoxib on TAC-induced cardiac remodeling. DM-celecoxib inhibited left ventricular systolic functional deterioration, and prevented left ventricular hypertrophy and fibrosis. It also activated GSK-3α and β by inhibiting Akt, suppressing the activity of β-catenin and nuclear factor of activated T-cells and thereby decreasing the expression of the Wnt/β-catenin target gene products fibronectin and matrix metalloproteinase-2. These results suggest that DM-celecoxib is clinically useful for treating pressure-induced heart diseases.

DOI： 10.1038/hr.2016.122

Language：English   Publishing type：Research paper (scientific journal)  

We previously reported that celecoxib, a selective COX-2 inhibitor, strongly inhibited human colon cancer cell proliferation by suppressing the Wnt/β-catenin signaling pathway. 2,5-Dimethylcelecoxib (DM-celecoxib), a celecoxib analog that does not inhibit COX-2, has also been reported to have an antitumor effect. In the present study, we elucidated whether DM-celecoxib inhibits intestinal cancer growth, and its underlying mechanism of action. First, we compared the effect of DM-celecoxib with that of celecoxib on the human colon cancer cell lines HCT-116 and DLD-1. 2,5-Dimethylcelecoxib suppressed cell proliferation and inhibited T-cell factor 7-like 2 expression with almost the same strength as celecoxib. 2,5-Dimethylcelecoxib also inhibited the T-cell factor-dependent transcription activity and suppressed the expression of Wnt/β-catenin target gene products cyclin D1 and survivin. Subsequently, we compared the in vivo effects of celecoxib and DM-celecoxib using the Mutyh^−/− mouse model, in which oxidative stress induces multiple intestinal carcinomas. Serum concentrations of orally administered celecoxib and DM-celecoxib elevated to the levels enough to suppress cancer cell proliferation. Repeated treatment with celecoxib and DM-celecoxib markedly reduced the number and size of the carcinomas without showing toxicity. These results suggest that the central mechanism for the anticancer effect of celecoxib derivatives is the suppression of the Wnt/β-catenin signaling pathway but not the inhibition of COX-2, and that DM-celecoxib might be a better lead compound candidate than celecoxib for the development of novel anticancer drugs.

DOI： 10.1111/cas.13106

Language：English   Publishing type：Research paper (scientific journal)  

A new hetero[7]helicene 1_NN structured by a diazabenzodiheterole (pyrroloindole) ring core was successfully synthesized by catalytic domino cyclodehydrogenation with Pd(OAc)₂ and O₂ as the key step. Significantly, 1_NN was stereochemically stable at room temperature and could be subjected to optical resolution by chiral HPLC. Furthermore, kinetic analysis of 1_NN and DFT calculations on its variants revealed that the stereo-chemical stability of the benzodiheterole-based helicenes was highly dependent on not only the heteroaromatic ring component but also on the N-substituent of the pyrrole ring unit.

DOI： 10.1246/cl.170410

Language：English   Publishing type：Research paper (scientific journal)  

A μ-oxo-dinuclear iron complex of a supramolecular porphyrin–phthalocyanine conjugate was synthesized and its catalytic electrochemical oxygen reduction properties were investigated. In the conjugate, porphyrin and phthalocyanine units were connected to form a cofacial dimeric structure through a flexible fourfold rotaxane linkage, which was advantageous for accommodating small substrates between the iron centers. The conjugate showed efficient catalytic properties, at more positive potentials than those of other reported dinuclear porphyrinoid iron complexes, to selectively afford water through a four-electron reduction process.

DOI： 10.1002/chem.201700082

Language：English   Publishing type：Research paper (scientific journal)  

A series of novel optically active [5]helicene-derived phosphine ligands (L1, with a 7,8-dihydro[5]helicene core structure- and L2, with a fully aromatic [5]helicene core structure) were synthesized. Despite their structural similarities, L1 and L2 exhibit particularly different characteristics in their use as chiral ligands. L1 was highly effective in the asymmetric allylation of indoles with 1,3-diphenylallyl acetate (up to 99% ee), and in the etherification of alcohols (up to 96% ee). In contrast, L2 was highly effective in the stereocontrol of helical chirality in Suzuki-Miyaura coupling (SMC) reaction (up to 99% ee). Density functional theory analysis was employed to propose a model that accounts for the origin of the enantioselectivity in these reactions.

DOI： 10.1038/srep36211

Language：English   Publishing type：Research paper (scientific journal)  

A variety of functionalized silacyclopentanes were synthesized by highly enantioselective β-eliminations of silacyclopentene oxides followed by stereospecific transformations. The reaction mechanism of the β-elimination was elucidated by DFT calculations. An in vitro biological assay with an oxy-functionalized silacyclopentane showed substantial binding to a serotonin receptor protein.

DOI： 10.1002/anie.201511728

Language：English   Publishing type：Research paper (scientific journal)  

Thiazolobenzyne, which is a benzyne species fused with a thiazole ring, was efficiently generated via an iodine-magnesium exchange reaction of an ortho-iodoaryl triflate-type precursor using a trimethylsilylmethyl Grignard reagent as an activator. A wide range of arynophiles reacted efficiently with the thiazolobenzynes generated by this method to afford various multisubstituted benzothiazoles.

DOI： 10.1039/c6cc05112j

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/jacs.5b10557

Language：English   Publishing type：Research paper (scientific journal)  

DOI： http://dx.doi.org/10.3998/ark.5550190.p009.069

Language：English   Publishing type：Research paper (scientific journal)  

We describe the synthesis, stereochemical characteristics, and coordination behavior of 2,2'-binaphtyl-1,1'-biisoquinoline (BINIQ), a new axially chiral bidentate ligand. BINIQ was obtained in a racemic form by the diastereoselective Ullmann coupling of 1-(2-iodonaphthalen-1-yl)isoquinoline, which was prepared by the regioselective C-H iodination of 1-(1-naphthyl)isoquinoline. BINIQ has three chiral biaryl axes α and γ at the two naphthylisoquinoline and β at the 2,2'-binaphthyl sites and their relative configuration (αR_aβR_a , γ_a ) in solid state was confirmed by X-ray diffraction analysis. The naphthyl-isoquinoline axes α and γ were proven rigid enough in solution to allow for optical resolution by a chiral HPLC method and a solution of the optically pure BINIQ (98% ee) in chloroform-d did not result in racemization while standing at room temperature for 24 h. On the other hand, the 2,2'-binaphthyl axis is stereochemically labile and readily alternates between βR_a and βS_a at room temperature. Accordingly, (αR_{a a} γ_a )- and (αR_{a a} ,γR_a)-BINIQ are in equilibrium in solution with the former stereoisomer being dominant, though the latter is suitable as a bidentate ligand. Notably, this dynamic stereochemical behavior enabled BINIQ to readily give the relative configuration (αR_{a a} ,γR_a ) upon coordination to a copper(I) ion at room temperature.

DOI： 10.3998/ark.5550190.p009.069

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/j.bcp.2014.03.006

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/jp408269s

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/j.tetlet.2013.10.080

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1246/cl.130411

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1246/cl.2011.1343

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/ol2025873

Language：English   Publishing type：Research paper (scientific journal)  

Celecoxib, a cyclooxygenase-2 (COX-2)-selective nonsteroidal anti-inflammatory drug, has been shown to inhibit Akt and prevent cardiac remodeling in aortic banding-induced failing heart in mice. However, it may be difficult to use celecoxib for the treatment of heart failure because of thromboembolic adverse reactions. Since 2,5-dimethyl (DM)-celecoxib, a derivative unable to inhibit COX-2, has been also reported to inhibit Akt, we attempted to examine whether DM-celecoxib retains the ability to prevent cardiac remodeling and improve cardiac functions using a mouse model of inherited dilated cardiomyopathy (DCM). DM-celecoxib as well as celecoxib administered daily for 4 weeks inhibited Akt and subsequent phosphorylation of glycogen synthase kinase-3β and mammalian target of rapamycin. Furthermore, both celecoxib and DM-celecoxib inhibited the activities of nuclear factor of activated T cell and -catenin and the expression of TCF7L2 (T-cell-specific transcriptional factor-7L2) and c-Myc, downstream mediators related to cardiac hypertrophy. Functional and morphological measurements showed that these compounds improved left ventricular systolic functions (ejection fraction: vehicle, 34.7 ± 3.9%; 100 mg/kg celecoxib, 50.3 ± 1.1%, p < 0.01; 100 mg/kg DM-celecoxib, 49.8 ± 0.8%, p < 0.01), which was also evidenced by the decrease in β-myosin heavy chain and B-type natriuretic peptide, and prevented hypertrophic cardiac remodeling (heart/body weight ratio: vehicle, 10.4 ± 0.7 mg/g; 100 mg/kg celecoxib, 8.0 ± 0.3 mg/g, p < 0.01; 100 mg/kg DM-celecoxib, 8.2 ± 0.1 mg/g, p < 0.05). As a consequence, both compounds improved the survival rate (vehicle, 45%; 100 mg/kg celecoxib, 75%, p < 0.05; 100 mg/kg DM-celecoxib, 70%, p < 0.05). These results suggested that not only celecoxib but also DM-celecoxib prevents cardiac remodeling and reduces mortality in DCM through a COX-2-independent mechanism involving Akt and its downstream mediators.

DOI： 10.1124/jpet.111.179325

Language：English   Publishing type：Research paper (scientific journal)  

DOI： doi:10.1124/jpet.111.179325.

Language：English   Publishing type：Research paper (scientific journal)  

The planar chiral diolefinic organonitrogen cycles 1 underwent stereospecific and group-selective olefin exchange with 3 to give 4, whose molecular structure was characterized on the basis of NMR and X-ray diffraction. The bonded (E)-olefin moieties in 4 were robust enough to allow untouched (Z)-olefin to undergo epoxidation and hydrogenation to give the corresponding PtCl₂(n²-olefin) complexes, whose treatment with PPh ₃ smoothly liberated their olefinic parts, which would be otherwise difficult to synthesize.

DOI： 10.1021/om1009704

Language：English   Publishing type：Research paper (scientific journal)  

Enantioselective synthesis of a planar chiral organonitrogen cycle has been newly developed based on the unprecedented prochiral face-selective cyclization of achiral linear precursors by an appropriate chiral promoter.

DOI： 10.1021/ja1024657

Language：English   Publishing type：Research paper (scientific journal)  

Sila analogues: The first asymmetric synthesis of silacarboxylic acids with a stereogenic center at the silicon atom has been achieved from chiral nonracemic silanols, without loss of optical purity. Silacarboxylic acids can be converted into their corresponding esters using a Mitsunobu-type reaction.

DOI： 10.1002/anie.200904922

Language：English   Publishing type：Research paper (scientific journal)  

Newly synthesized 9-membered diallylic organosulfur cycles have proven to possess planar chirality originating from the rigidity of their medium-sized cyclic structure. The oxidation state of the sulfur atom significantly influences their stereochemical behavior as well as their reactivity.

DOI： 10.1246/cl.2009.1028

Language：English   Publishing type：Research paper (scientific journal)  

An enantioselective nucleophilic substitution reaction of achiral dialkoxysilane has been developed. The reaction proceeds with efficient stereocontrol on the silicon chirality center to give the enantioenriched silyl ether, which can be converted to the silanol without loss of enantiopurity. We have analyzed the steric course of the reaction by using DFT calculations and propose a transition state model to explain the observed enantioselectivity.

DOI： 10.1021/ja805848z

Language：English   Publishing type：Research paper (scientific journal)  

Both enantiomers of kainic acid have been synthesized from enantioenriched planar chiral cyclic amide 2a. The C3 and C4 stereocenters in the pyrrolidine ring were constructed by transannular Cope rearrangement of 2a, and the carboxyl group at the C2 position was introduced through lithiation followed by a carboxylation in the presence of an external chiral ligand.

DOI： 10.1016/j.tetlet.2008.08.058

Language：English   Publishing type：Research paper (scientific journal)  

An efficient approach to nine-membered diallylic cyclic amides having a variety of substituents has been developed. The synthesized amides have stable planar chirality at ambient temperature. The transformation of the enantiomerically enriched amides provides optically active compounds containing stereogenic centers in a stereospecific fashion. As a demonstration of the synthetic utility of the amides, we have synthesized (+)-γ-lycorane using such an optically active amide as a chiral building block.

DOI： 10.1055/s-2008-1078235

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

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Responsible for pages：18巻，7-59項   Language：Japanese   Book type：Scholarly book

Language：English   Book type：Scholarly book

Responsible for pages：Enantioselective Synthesis by Lithiation Adjacent to O and Subsequent Rearrangement   Language：English   Book type：Scholarly book

Responsible for pages：第６版   Language：Japanese   Book type：Scholarly book

Event date： 2021.6

Language：Japanese   Presentation type：Oral presentation (general)  

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Venue：名古屋   Country：Japan  

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Venue：名古屋   Country：Japan  

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Venue：名古屋   Country：Japan  

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Venue：船橋   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：船橋   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：船橋   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：船橋   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：東京   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：横浜   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：熱海   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：守山   Country：Japan  

Language：English   Presentation type：Oral presentation (general)  

Venue：Kaohsiung   Country：Taiwan, Province of China  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：三田   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：田辺（同志社大学・京田辺キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：田辺（同志社大学・京田辺キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：田辺（同志社大学・京田辺キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：田辺（同志社大学・京田辺キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：田辺（同志社大学・京田辺キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：田辺（同志社大学・京田辺キャンパス）   Country：Japan  

Language：English   Presentation type：Oral presentation (general)  

Venue：大阪（コングレコンベンションセンター）   Country：Japan  

Language：English   Presentation type：Oral presentation (general)  

Venue：大阪（コングレコンベンションセンター）   Country：Japan  

Language：English   Presentation type：Oral presentation (general)  

Venue：大阪（コングレコンベンションセンター）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：名古屋（名古屋大学）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：名古屋（名古屋大学）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：名古屋（名古屋大学）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：北九州（北九州国際会議場）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：北九州（北九州国際会議場）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：福岡（九州大学伊都キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：福岡（九州大学伊都キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：松山市（にぎたつ会館）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：松山市（にぎたつ会館）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：松山市（にぎたつ会館）   Country：Japan  

Language：English   Presentation type：Oral presentation (general)  

Venue：Fukuoka (Kyushu University)   Country：Japan  

Language：English   Presentation type：Oral presentation (general)  

Venue：Fukuoka (Kyushu University)   Country：Japan  

Language：English   Presentation type：Oral presentation (general)  

Venue：Deajeon (KAIST)   Country：Korea, Republic of  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：廿日（安芸グランドホテル）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：府中（東京農工大学）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：札幌（北海道大学）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：札幌（北海道大学）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：横浜（慶應義塾大学日吉キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：横浜（慶應義塾大学日吉キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：横浜（慶應義塾大学日吉キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：横浜（慶應義塾大学日吉キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：横浜（慶應義塾大学日吉キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：岡山（岡山大学津島キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：福岡（九州大学馬出キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：松山市（にぎたつ会館）   Country：Japan  

Language：English   Presentation type：Oral presentation (general)  

Venue：Stanford (Stanford University)   Country：United States  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：北九州（北九州国際会議場）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：北九州（北九州国際会議場）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：福岡（九州大学伊都キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：仙台（秋保温泉ホテルクレセント）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：仙台（秋保温泉ホテルクレセント）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：福岡（九州大学伊都キャンパス）   Country：Japan  

Language：English   Presentation type：Oral presentation (general)  

Venue：蘭州 (Lanzhou University)   Country：China  

Language：English   Presentation type：Oral presentation (general)  

Venue：西安 (Embassador International Hotel)   Country：China  

Language：English   Presentation type：Oral presentation (general)  

Venue：上海 (Shanghai Institute of Organic Chemistry)   Country：China  

Language：English   Presentation type：Oral presentation (general)  

Venue：上海 (Shanghai Institute of Materia Medica)   Country：China  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：東京（東京工業大学大岡山キャンパス）   Country：Japan  

Language：English   Presentation type：Oral presentation (general)  

Venue：Kasuga (Kyushu University)   Country：Japan  

Language：English   Presentation type：Oral presentation (general)  

Venue：Kasuga (Kyushu University)   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：船橋（日本大学船橋キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：船橋（日本大学船橋キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：船橋（日本大学船橋キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：船橋（日本大学船橋キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：船橋（日本大学船橋キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：船橋（日本大学船橋キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：船橋（日本大学船橋キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：船橋（日本大学船橋キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：福岡（九州大学馬出キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：北九州（北九州国際会議場）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：名古屋（名古屋大学）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：久留米（久留米シティプラザ）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：福岡（九州大学馬出キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：春日（九州大学筑紫キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：春日（九州大学筑紫キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：春日（九州大学筑紫キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：春日（九州大学筑紫キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：春日（九州大学筑紫キャンパス）   Country：Japan  

Language：English   Presentation type：Oral presentation (general)  

Venue：福岡（九州大学馬出キャンパス）   Country：Japan  

Language：English   Presentation type：Oral presentation (general)  

Venue：仙台（東北大学）   Country：Japan  

Language：English   Presentation type：Oral presentation (general)  

Venue：Hsinchu   Country：Taiwan, Province of China  

Language：English   Presentation type：Oral presentation (general)  

Venue：京都 (京都大学桂キャンパス)   Country：Japan  

Language：English   Presentation type：Oral presentation (general)  

Venue：Bangkok   Country：Thailand  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：三田（関西学院大学三田キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：福岡（九州大学馬出キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：鳥取（鳥取大学）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：岡本（甲南大学岡本キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：岡本（甲南大学岡本キャンパス）   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：岡本（甲南大学岡本キャンパス）   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：東京   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：東京都，タワーホール船堀   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：東京都，東京大学   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：大阪府吹田市，大阪大学コンベンションセンター   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：広島県安芸市，安芸グランドホテル   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：徳島県   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：新潟県，長岡市，長岡技術科学大学   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：新潟県，長岡市，長岡技術科学大学   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：東京都，早稲田大学   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：東京都，日本薬学会長井記念ホール   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：京都市，京都薬科大学   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：Honolulu, Hawaii, USA   Country：United States  

Presentation type：Oral presentation (general)  

Venue：日本大学理工学部船橋キャンパス   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：日本大学理工学部船橋キャンパス   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：日本大学理工学部船橋キャンパス   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：日本大学理工学部船橋キャンパス   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：日本大学理工学部船橋キャンパス   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：日本大学理工学部船橋キャンパス   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：埼玉大学工学部   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：埼玉大学工学部   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：京都   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：沖縄   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：東京都，北里大学   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：台湾，精華大学   Country：Taiwan, Province of China  

Presentation type：Oral presentation (general)  

Venue：台湾，精華大学   Country：Taiwan, Province of China  

Presentation type：Oral presentation (general)  

Venue：東京都，早稲田大学   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：東京都，東京大学   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：新潟大学   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：関西大学千里山キャンパス   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：関西大学千里山キャンパス   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：関西大学千里山キャンパス   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：関西大学千里山キャンパス   Country：Japan  

Presentation type：Oral presentation (general)  

Venue：関西大学千里山キャンパス   Country：Japan  

Event date： 2023.12

Language：English  

Country：Japan  

Event date： 2023.12

Language：Japanese  

Country：Japan  

Event date： 2023.11

Language：Japanese  

Country：Japan  

Event date： 2023.11 - 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.10

Language：English  

Country：France  

Event date： 2023.10 - 2024.10

Language：English  

Country：Japan  

Event date： 2023.9 - 2024.9

Language：Japanese  

Country：Japan  

Event date： 2023.8 - 2024.8

Language：Japanese  

Venue：慶應義塾大学 矢上キャンパス   Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2023.5

Language：Japanese  

Country：Japan  

Event date： 2022.9 - 2023.9

Language：Japanese  

Country：Japan  

Event date： 2022.9 - 2024.9

Language：Japanese  

Country：Japan  

Event date： 2022.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン開催   Country：Japan  

Event date： 2022.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン開催   Country：Japan  

Event date： 2022.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン開催   Country：Japan  

Event date： 2022.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン開催   Country：Japan  

Event date： 2021.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン開催   Country：Japan  

Event date： 2021.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン開催   Country：Japan  

Event date： 2021.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン開催   Country：Japan  

Event date： 2021.3

Language：English   Presentation type：Oral presentation (general)  

Venue：オンライン開催   Country：Japan  

Event date： 2021.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン開催   Country：Japan  

Event date： 2020.12

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：北海道大学 フロンティア化学教育研究センター   Country：Japan  

Event date： 2020.11 - 2020.12

Language：Japanese   Presentation type：Public lecture, seminar, tutorial, course, or other speech  

Venue：北海道大学 フロンティア化学教育研究センター   Country：Japan  

Event date： 2020.11

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：京都大学薬学部   Country：Japan  

Event date： 2020.9

Language：Japanese   Presentation type：Public lecture, seminar, tutorial, course, or other speech  

Venue：オンライン開催   Country：Japan  

Event date： 2020.6

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：オンライン開催   Country：Japan  

Event date： 2014.4

Language：English   Presentation type：Oral presentation (general)  

Venue：National Tsing Hua University, Hsinchu   Country：Taiwan, Province of China  

Event date： 2013.9

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：横浜   Country：Japan  

Event date： 2012.3

Presentation type：Oral presentation (general)  

Venue：横浜   Country：Japan  

Event date： 2012.3

Presentation type：Oral presentation (general)  

Venue：横浜   Country：Japan  

Event date： 2011.11

Presentation type：Oral presentation (general)  

Venue：東京   Country：Japan  

Event date： 2011.11

Presentation type：Oral presentation (general)  

Venue：東京   Country：Japan  

Event date： 2011.10

Presentation type：Oral presentation (general)  

Venue：神戸   Country：Japan  

Event date： 2011.9 - 2011.10

Presentation type：Oral presentation (general)  

Venue：Gyeongju   Country：Korea, Republic of  

Event date： 2011.9

Presentation type：Oral presentation (general)  

Venue：名古屋   Country：Japan  

Event date： 2011.8

Presentation type：Oral presentation (general)  

Venue：福岡   Country：Japan  

Event date： 2011.7

Presentation type：Oral presentation (general)  

Venue：神戸   Country：Japan