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Mitsuru Shindo Last modified date:2024.05.01

Professor / Interdisciplinary Graduate School of Engineering Sciences
Department of Fundamental Organic Chemistry
Institute for Materials Chemistry and Engineering

Graduate School
Undergraduate School

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 Reseacher Profiling Tool Kyushu University Pure
Academic Degree
Ph. D.
Field of Specialization
Synthetic Organic Chemistry,Chemical Biology
Total Priod of education and research career in the foreign country
Research Interests
  • Ultraviolet absorption reagents based on natural products.
    keyword : ultraviolet, natural product, UV-A, absorption reagent
  • Synthesis and application of iptycenes
    keyword : triptycene, iptycene, ynolate, aryne, distortion, secondary orbital interaction, triple addition
  • Catalytic Oxidative Coupling reaction
    keyword : catalyst, C-H activation, coupling reaction, aerobic oxidation
  • Synthesis and Chemical Biology studies on anti-tumor active compounds
    keyword : synthesis, chemical biology, anti-tumor, natural products
  • Total synthesis of bioactive alkaloids
    keyword : Total synthesis, bioactivity, stemona alkaloid
  • Novel matrix for MALDI-MS
    keyword : matrix, MALDI-MS
  • Plant regulation reagents derived from allelochemicals
    keyword : allelopathy, total synthesis, chemical biology, natural organic coupounds, structure-activity relationship, bioprobe, agrochemicals, gravitropism
  • Development of novel carbon dianion reactive species and thier successive reactions
    keyword : dianions, successive reactions, electrocyclization
  • Novel catalytic Nazarov reaction and its synthetic applications for preparation of bioactive compounds
    keyword : Nazarov reaction, acid catalysts, bioactive compounds, total synthesis, asymmetric reactions
  • Catalytic Wittig Lactonization
    keyword : metal catalysts, acylation, phosphorous ylids, Wittig reaction, lactonization
  • chemistr of ynolates
    keyword : ynolates
    1996.08generation of ynolates, new reactions of ynolates, nucleophile-electrophile switching multi-process.
  • Synthesis and reactions of hypervalent compounds
    keyword : hypervalency, silicone, germanium, coupling reaction
    2003.04~2012.03Hypervalent silicone and germanium compounds formed by intramolecular coordination are designed and synthesized. Utilizing the bonds activated by the hypervalency, new bond forming reactions are developed..
Current and Past Project
Academic Activities
1. Mitsuru Shindo, Kenji Matsumoto, Metal catalyzed synthetic reactions via aerobic oxidation as a key step, Springer Singapore, 10.1007/978-981-10-3421-3_2, 11-27, 2017.01, New aerobic oxidative metal catalyzed synthetic reactions are described: The Cu(II) complex catalyzed the acylation of thioester in Wittig lactonization under neutral conditions and the dissymmetrization of symmetric dithiomalonates via selective monoacylation. The key step in this reaction was the formation of an acylketene, the stability of which would contribute to selectivity. The aerobic Rh/C-catalyzed oxidative homo- and cross-coupling of aryl amines was developed. The coupling reactions afforded symmetrical and nonsymmetrical biaryl amines in excellent yields. These reactions provide a mild, operationally simple, and efficient approach for the synthesis of biaryls which are important to pharmaceutical and materials chemistry..
2. 新藤 充, 松本 健司,
Stereoselective Synthesis of Tetrasubstituted Alkenes via Torquoselectivity-Controlled Olefination of Carbonyl Cmpounds with Ynolates,in Top. Curr. Chem.
, Springer, 327, 1-32 , 2012.01.
3. Mitsuru Shindo, The chemistry of metal ynolates (in The Chemistry of Metal Enolates, Patai series), John Wiley & Sons, Chapter 13, 2009.08.
1. Mitsuru Shindo, Takayuki Iwata , Cycloaddition Initiated by Ynolates: High-Energy Dianion Equivalents as a Molecular Glue, Synlett, 2022.01.
2. Takayuki Iwata, Mitsuru Shindo, Synthesis of 1,8,13-substituted triptycenes, Chemistry Letters, 2020.11.
3. Takayuki Iwata, Mitsuru Shindo, Synthesis, Stereochemical Stability, and Biological Activity of Stemonamine and Its Related Stemona Alkaloids, Heterocycles, 10.3987/REV-19-902, 98 (3), 349-377 (2019)., 2019.03.
4. Mitsuru Shindo, Kenji Matsumoto, 'Recent Advances in the Chemistry of Metal Ynolates' , the Chemistry of Metal Ynolates' in Patai's Chemistry of Functional Groups. 1–31., edited by J. Zabicky. John Wiley & Sons, Ltd: Chichester, UK., 2016.05, Recent adavances on ynolate chemistry was reviewed..
5. Mitsuru Shindo, Seiji Mori,, Torquoselective Olefination of Caronyl Compounds via Ynolates. Highly Efficient Stereoselective Synthesis of Tetrasubstituted Alkenes, Synlett, 2231-2243, 2008.09.
6. torquoselective olefination with ynolates.
7. 新藤充, Synthetic uses of Ynolates, Tetrahedron, 63, 10-16, 2007.01.
8. M. Shindo, Ynolates as Functional Carbanions, Synthesis, 2275-2288, 2003.01.
1. Iwata Takayuki; #Funatsu Shingo; Shindo Mitsuru, , Nazarov Reaction Triggered by Active Lithium Salts in Cyclopentyl Methyl Ether, Chem Lett,, in press, 2024.03.
2. Takayuki Iwata, Mizuki Hyodo, Ryusei Kawano, Mitsuru Shindo, A Strategy based on “Ambident Anthracene” for the Synthesis of Higher-Order Iptycenes e202303687 (2023).【hot paper】, Chem. Eur. J. ,, e202303687, 2024.03, アラインと求アラインの両者の性質を併せ持つアンビデントアントラセンを用いたイプチセンの一般的構築法を見出した。これを用いて史上最長の直鎖型イプチセンの合成に成功した。.
3. Iwata Takayuki; #Funatsu Shingo; #Kajiwara Kohei; Shiota Yoshihito; Yoshizawa Kazunari; Shindo Mitsuru, , Neutral Nazarov Reaction Using Protic Solvents as Activators, , Bull Chem Soc Jpn,, in press, 2024.01.
4. Takayuki Iwata, Masato Hanada, Satoru Kumagai, Tatsuro Yoshinaga, Yoshihito Shiota, Kazunari Yoshizawa, Mitsuru Shindo, Intramolecular Hiyama Coupling: Synthesis of 1,8,13-Trisubstituted Chiral Triptycenes with Three Different Substituents by Intramolecular Substituent Transfer, Chemistry European Journal,, 29, e202300988, 2023.04, トリプチセン上で分子内檜山カップリングに成功した。この手法によりキラルトリプチセンの合成に成功した。.
5. Takeshi Nishimura, Saki Makigawa, Jun Sun, Kozue Kodama, Hiromi Sugiyama, Kenji Matsumoto, Takayuki Iwata, Naoya Wasano, Arihiro Kano, Miyo Terao Morita, Yoshiharu Fujii, Mitsuru Shindo,, Design and synthesis of strong root gravitropism inhibitors with no concomitant growth inhibition, Scientific Reports,, 13, 5173, 2023.03, 植物根に対する強力な重力屈性阻害剤BMAを開発した。成長抑制や毒性を示さない選択的な阻害剤で、従来品の中でももっとも強力な阻害剤である。植物生理学実験で、植物ホルモンのオーキシンの極性輸送に関わることが判明し、それも従来の阻害剤とは異なる機構であることも判明した。今後、環境に優しい緑化調節剤や抑草剤としての応用が期待される。.
6. Takayuki Iwata; Mizuki Hyodo, Takumi Fujiwara, Leah Kuhn, Igor V. Alabugin, Mitsuru Shindo,, 3-Trifluoromethylbenzyne: Precise Orientation in Cycloaddition Reaction Enabled Regioselective Synthesis of Trifluoromethylated Triptycenes, Synthesis, 10.1055/a-1818-0576, 54, 22, 4971-4978, 2022.04.
7. Takayuki Iwata, Ryusei Kawano, Takuto Fukami, Mitsuru Shindo, Retro-Friedel–Crafts-type Acidic Ring-Opening of Triptycenes: A New Synthetic Approach to Acenes, Chemistry-A Europian Journal,, 2022.01, トリプチセンの酸による新規開環反応を見出した。本反応を応用して、有機電子材料として重要なアセンの合成に成功した。.
8. Takayuki Iwata, Satoru Kumagai, Tatsuro Yoshinaga, Masato Hanada, Yoshihito Shiota, Kazunari Yoshizawa, Mitsuru Shindo,, Quadruple Role of Pd Catalyst in Domino Reaction Involving Aryl to Alkyl 1,5-Pd Migration to Access 1,9-Bridged Triptycenes, CHEMISTRY-A EUROPEAN JOURNAL, 10.1002/chem.202101728, 27, 45, 11548-11553, 2021.08, パラジウム触媒による新規4連続反応を見出し、キラルトリプチセンの合成に成功した。本反応では一つのパラジウム触媒が酸化的付加に引き続く炭素水素結合切断反応による還元反応、環化反応、鈴木カップリング、アリルホウ酸のホモカップリングという4種の異種反応を触媒していることを理論計算により明らかにした。。.
9. Iwata, Takayuki; Yoshinaga, Tatsuro; Shindo, Mitsuru, Flow Synthesis of Triptycene via Triple Cycloaddition of Ynolate to Benzyne, SYNLETT, 10.1055/s-0040-1706417, 31, 19, 1903-1906, 2020.12.
10. Shindo, Mitsuru; Makigawa, Saki; Kodama, Kozue; Sugiyama, Hiromi; Matsumoto, Kenji; Iwata, Takayuki; Wasano, Naoya; Kano, Arihiro; Morita, Miyo Terao; Fujii, Yoshiharu, Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity, PHYTOCHEMISTRY, 10.1016/j.phytochem.2020.112508, 179, 112508, 2020.11.
11. Jun Sun, Takayuki Iwata, Mitsuru Shindo, Synthesis of 9-hydroxytriptycenes bearing a functionalized substituent at the C-10 position through a triple cycloaddition reaction of ynolates derived from 2,6-di-tert-butylphenyl esters., Chemistry Letters,, 49, in press, 2020.07.
12. Iwata, Takayuki; Hyodo, Mizuki; Fukami, Takuto; Shiota, Yoshihito; Yoshizawa, Kazunari; Shindo, Mitsuru, Anthranoxides as Highly Reactive Arynophiles for the Synthesis of Triptycenes, CHEMISTRY-A EUROPEAN JOURNAL, 10.1002/chem.202002065, 26, 39, 8506-8510, 2020.07, We report herein an efficient method to synthesize triptycenes by the reaction of benzynes and anthranoxides, which are electron-rich and readily prepared from the corresponding anthrones. Using this method, 1,9-syn-substituted triptycenes were regioselectively obtained employing 3-methoxybenzynes. This method was also applied to synthesize pentiptycenes. A DFT study revealed that the cycloaddition of lithium anthranoxide and benzyne proceeds stepwise..
13. Mitsuru Shindo, Saki Makigawa, Kenji Matsumoto, Takayuki Iwata, Naoya Wasano, Arihiro Kano, Miyo Terao Morita, Yoshiharu Fujii, Essential structural features of (2Z,4E)-5-phenylpenta-2,4-dienoic acid for inhibition of root gravitropism, Phytochemistry, 10.1016/j.phytochem.2020.112287, 172, 2020.04, Previously, we found (2Z,4E)-5-phenylpenta-2,4-dienoic acid (ku-76) to be a selective inhibitor of root gravitropic bending of lettuce radicles at 5 μM, with no concomitant growth inhibition. Here, we describe a structure-activity relationship study of ku-76 to determine the essential structural features for the inhibitory activity. A series of ku-76 analogues was synthesized and the key features of ku-76 that are necessary for inhibition of lettuce root gravitropic bending were determined. The (2E,4E)-, (2Z,4Z)- (2E,4Z)- analogues were inactive, and 4,5-saturated and 4,5-alkynyl analogues also did not show inhibitory activity, demonstrating the importance of the (2Z,4E) diene unit. The aromatic ring was also crucial and could not be replaced with an alkyl chain. Derivatives in which the carboxylic acid was replaced with amides, alcohols, or esters were much less potent. These results suggest that the (2Z,4E)-diene, the carboxylic acid moiety, and the aromatic ring are essential for potent inhibitory activity against gravitropic bending..
14. Tatsuro Yoshinaga, Takayuki Iwata, Mitsuru Shindo, Mild environment-friendly oxidative debenzylation of N-benzylanilines using DMSO as an oxidant, Chemistry Letters, 10.1246/cl.190854, 49, 2, 191-194, 2020.01, Oxidative debenzylation of N-benzyl aromatic amines using DMSO as a non-toxic oxidant and catalyzed by TsOH gave Nphenylimines, which were spontaneously hydrolyzed to form anilines and benzaldehydes in good yields. This reaction employs mild, metal-free conditions. The conditions are also suitable for the debenzylation of benzylphenylethers..
15. Tatsuro Yoshinaga, Takumi Fujiwara, Takayuki Iwata, Mitsuru Shindo, Synthesis of Distorted 1,8,13-Trisilyl-9-hydroxytriptycenes by Triple Cycloaddition of Ynolates to 3-Silylbenzynes, Chemistry - A European Journal, 10.1002/chem.201903024, 25, 61, 13855-13859, 2019.11, 1,8,13-Trialkyl(aryl)silyl-9-hydroxytriptycenes (trisilyltriptycenes) were synthesized by the triple addition of ynolates and 3-silylbenzynes with high regioselectivity. Benzene rings in the resulting triptycenes were highly distorted where the dihedral angles between the substituents were as high as 35°. The distortion energy induced step-by-step halogenation reactions to yield halogenated triptycenes, including chiral triptycenes. The 1,8,13-trihalogenated triptycenes were then converted to 1,8,13-functionalized triptycenes..
16. Jun Sun, Toshiya Yoshiiwa, Takayuki Iwata, Mitsuru Shindo, Synthesis of Ynolates via Double Deprotonation of Nonbrominated Esters, Organic Letters, 10.1021/acs.orglett.9b02069, 21, 17, 6585-6588, 2019.09, Herein, we report a double deprotonation method used for the preparation of ynolates starting from nonbrominated 2,6-di-tert-butylphenyl esters. The current method is superior to the previously described double lithium/halogen exchange approach because easily accessible starting materials are used. This method will be especially useful for preparation of ynolates bearing functional groups in organic synthesis..
17. Takayuki Iwata, Taishi Tomiyama, Satoshi Fujita, Mitsuru Shindo, First Asymmetric Total Synthesis Of (−)-Isostemonamine And Kinetic Analysis Of Its Isomerizations, Heterocycles, 10.3987/COM-18-S(T)71, 97, 2, 712-718, 2018.04.
18. Satoshi Fujita, Masaki Suyama, Kenji Matsumoto, Atsushi Yamamoto, Takenori Yamamoto, Yuka Hiroshima, Takayuki Iwata, Arihiro Kano, Yasuo Shinohara, Mitsuru Shindo, Synthesis and evaluation of simplified functionalized bongkrekic acid analogs, Tetrahedron, 10.1016/j.tet.2018.01.018, 74, 9, 962-969, 2018.03, Bongkrekic acid (BKA) is a strong inhibitor of adenine nucleotide translocase (ANT), inducing inhibition of adenosine triphosphate synthesis. We designed and synthesized simplified benzene-ring-containing BKA analogs. The key reaction is the one-pot double Sonogashira reaction, which forms the main skeleton. The analogs were efficiently synthesized in 8–10 longest linear sequence steps. This synthetic method can be applied for the preparation of other analogs having different combinations of carbon chain lengths. Furthermore, the allyloxy group on the benzene ring can be easily replaced by other functional groups. Our preliminary biological evaluation based on mitochondrial inhibitory effects revealed the high potency of the analogs bearing the same carbon chain length as that of BKA. In particular, the prefunctionalized analogs are potential ANT inhibitors..
19. Satoshi Fujita, Keisuke Nishikawa, Takayuki Iwata, Taishi Tomiyama, Hiroshi Ikenaga, Kenji Matsumoto, Mitsuru Shindo, Asymmetric Total Synthesis of (−)-Stemonamine and Its Stereochemical Stability, Chemistry - A European Journal, 10.1002/chem.201706057, 24, 7, 1539-1543, 2018.02, The first asymmetric total synthesis of (−)-stemonamine is described. The key reactions included intramolecular acylation to construct the seven-membered ring and a tandem [2+2] cycloaddition-Dieckmann condensation reaction using an ynolate to form the fully substituted cyclopentenone moiety. Racemization and epimerization of the natural product were first experimentally demonstrated..
20. Kenji Matsumoto, Naoyuki Mizushina, Masahiro Yoshida, Mitsuru Shindo, Stereocontrolled Synthesis of Multisubstituted 1,3-Dienes via an Allene-Claisen Rearrangement, Synlett, 10.1055/s-0036-1590970, 28, 17, 2340-2344, 2017.10, We herein developed a stereoselective synthetic method for the preparation of multisubstituted 1,3-dienes via an allene-Claisen rearrangement. The Claisen rearrangement of anti -allenyl alcohols provided (1 E,3 Z)-1,3-dienes, which are essential components of bongkrekic acid, in high stereoselectivities. To demonstrate the synthetic utility of the resulting 1,3-dienes, further functional transformations and Diels-Alder reactions are described..
21. Kenji Matsumoto, Shohei Tachikawa, Noriko Hashimoto, Rina Nakano, Masahiro Yoshida, Mitsuru Shindo, Aerobic C-H Oxidation of Arenes Using a Recyclable, Heterogeneous Rhodium Catalyst, Journal of Organic Chemistry, 10.1021/acs.joc.7b00300, 82, 8, 4305-4316, 2017.04, A novel, practical protocol for the aerobic direct C-H acetoxylation of arenes, employing a recyclable heterogeneous rhodium catalyst, is reported herein. The trifluoroacetoxylation of 2-amido-substituted anthracenes proceeded at the 9-position with exclusive regioselectivity. The oxidation of variously substituted anthracenes and other polycyclic aromatics with molecular oxygen as a terminal oxidant proceeded under mild conditions, providing products in good to excellent yields..
22. 新藤 充, Shigenobu Fujimoto, kenji matsumoto, Aerobic oxidative homocoupling reaction of anilides using heterogeneous metal catalysts, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2017.01.075, 58, 10, 973-976, 2017.03.
23. Hisashi Wauke, Kazumasa Matsuo, kenji matsumoto, 新藤 充, Synthesis of Dissymmetric Malonic Acid Monoamides from Symmetric Dithiomalonates,, ChemistrySelect , 1, 21, 6830-6833, 2017.01.
24. Satoshi Umezu, Gomes, Gabriel dos Passos, Tatsuro Yoshinaga, Mikei Sakae, kenji matsumoto, Takayuki IWATA, Igor Alabugin, 新藤 充, Regioselective One-Pot Synthesis of Triptycenes via Triple-Cycloadditions of Arynes to Ynolates, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 10.1002/anie.201609111, 56, 5, 1298-1302, 2017.01, We developed the novel one-pot synthetic method of substituted triptycenes by the reaction of ynolates and arynes. This four-step process involves three cycloadditions and electrocyclic ring opening of the strained Dewar anthracene. Each of the three related but structurally distinct classes of nucleophiles (ynolate, enolate and anthracenolate) reacts with o-benzyne in the same predictable manner controlled by chelation and negative hyperconjugation. The resulting functionalized C3-symmetrical triptycenes hold promise in the design of functional materials..
25. 福田洋, 西川 慶祐, 福永 幸裕, 児玉梢, kenji matsumoto, 奥田 勝博, Arihiro Kano, 新藤 充, Synthesis of Fluorescent Molecular Probes Based on cis-Cinnamic acid and Molecular Imaging of Lettuce Roots, Tetrahedron, 印刷中, 2016.09.
26. 藤本茂伸, kenji matsumoto, 新藤 充, Aerobic Oxidative Intramolecular Aromatic Coupling via Heterogeneous Metal Catalysts,, Advanced Synthesis & Catalysis, 印刷中, 2016.07.
27. 松本 健司, 吉田まさひろ, 新藤 充, Heterogeneous Rhodium−Catalyzed Aerobic Oxidative Dehydrogenative Cross−Coupling Affording Nonsymmetrical Biaryl Amines, Angew. Chem. Int. Ed., 55, 17, 5272-5276, 2016.02, The first heterogeneously catalyzed oxidative C–H/C–H cross-coupling of aryl amines is reported herein. 2-Naphthyl amine analogs were reacted with various electron-rich arenes using a heterogeneous Rh/C catalyst under aerobic conditions, affording nonsymmetrical biaryl amines in excellent yields with high selectivities. This reaction provides a mild, operationally simple, and efficient approaches for the synthesis of biaryls that important to pharmaceutical and materials chemistry..
28. Yamamoto, Atsushi, はすいけいすけ, まつろひろし, 奥田 勝博, 安部真人, 松本 健司, はらだかずき, よしむらゆうや, 山本武範, おおくらかずと, 新藤 充, 篠原康雄, Bongkrekic Acid Analogue, Lacking One of the Carboxylic Groups of its Parent Compound, Shows Moderate but pH-insensitive Inhibitory Effects on the Mitochondrial ADP/ATP Carrier, CHEMICAL BIOLOGY & DRUG DESIGN, 10.1111/cbdd.12594, 86, 5, 1304-1322, 2015.11.
29. 松本 健司, 堂籠健斗, 太刀川祥平, 石井孝典, 新藤 充, Aerobic Oxidative Homocoupling of Aryl Amines Using Heterogeneous Rhodium Catalysts, , Org. Lett. 16, 4754-4757 (2014)., 16, 4754-4757, 2014.10.
30. 吉岩俊也, 梅津智, 渡慶次学, 馬場義信, 新藤 充, Synthesis and Reactions of Ynolates via a Stop-Flow Method with a Flow Microreactor, J. Flow Chemistry, 180-184, 4, 2014.10.
31. 奥田 勝博, 福田洋, 西川 慶祐, 新藤 充, cis-Cinnamic acid selective suppressors distinct from auxin inhibitors., Chem. Pharm. Bull., in press, 2014.06.
32. 梅津智, 吉岩俊也, 渡慶次学, 新藤 充, Generation of Ynolates via Reductive Lithiation Using Flow Microreactors, Tetrahedron Lett.,, 55, 1822-1825, 2014.01.
33. 西川 慶祐, 福田洋, 安倍真人, 中西一成, 谷口智也, 野村隆, 平館俊太郎, 藤井義晴, 奥田勝博, 新藤 充, Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors, PHYTOCHEMISTRY, 10.1016/j.phytochem.2013.08.013, 96, 132-147, 2013.12.
34. 梅津智, 新藤 充, alpha-Substituent Effect on Olefination of Ester Carbonyl Groups with Ynolates, Tetrahedron Lett ,, 54, 6871-6873, 2013.11.
35. 新藤 充, 松本 健司, Synthesis of Xanthanolides Including New Acylations and Their Synthetic Applications, J. Syn. Org. Chem. Japan, 71, 1152-1162, 2013.11.
36. 西川 慶祐, 福田洋, 安倍真人, 中西一成, 田澤雄太, 平館俊太郎, 藤井義晴, 奥田 勝博, 新藤 充, Design and Synthesis of Conformationally Constrained Analogues of cis-Cinnamic Acid and Evaluation of Their Plant Growth Inhibitory Activity, Phytochemistry,, 96, 223-234, 2013.10.
37. 松本 健司, 小谷内邦吉, 新藤充, Asymmetric total syntheses of xanthatin and 11,13-dihydroxanthatin using a stereocontrolled conjugate allylation to gamma-butenolide, TETRAHEDRON, 10.1016/j.tet.2012.11.077, 69, 3, 1043-1049, 2013.01.
38. 安倍真人, 西川 慶祐, 福田洋, 中西一成, 平館俊太郎, 藤井義晴, 奥田 勝博, 新藤 充, Key structural features of cis-cinnamic acid as an allelochemical, PHYTOCHEMISTRY, 10.1016/j.phytochem.2012.08.001, 84, 56-67, 2012.12.
39. 奥田 勝博, Keisuke Hasui, 松本 健司, Mitsuru Shindo, Molecular Design, Synthesis, and Evaluation of Novel Potent Apoptosis Inhibitors Inspired from Bongkrekic Acid, CHEMICAL RESEARCH IN TOXICOLOGY, 10.1021/tx300315h, 25, 10, 2253-2260, 2012.10.
40. 松本 健司, 新藤充, Palladium-Catalyzed Fluoride-Free Cross Coupling of Intramolecularly Activated Alkenylsilanes and Alkenylgermanes: Synthesis of Tamoxifen as a Synthetic Application,
, Adv. Synth. Catal., 354, 642-650 , 2012.01.
41. 松尾和真、西川慶介、新藤 充, Stereoselective synthesis of beta-glycosyl esters of cis-cinnamic acid and its derivatives using unprotected glycosyl donors, Tetrahedron Letters, in press, 2011.09.
42. 松尾和真、新藤 充, Efficient Synthesis of Dissymmetric Malonic Acid S,O-Esters via Mono-alcoholysis of Symmetric Dithiomalonates under Neutral Conditions, Organic Letters, 13, 4406-4409, 2011.09.
43. Kazumasa Matsuo, Mitsuru Shindo, Efficient Synthesis of Karrikinolide via Cu(II)-Catalyzed Lactonization, Tetrahedron, 10.1016/j.tet.2010.11.108, 67, 971-975, 2011.01.
44. Kentaro Yaji, Mitsuru Shindo, Total Synthesis of (±)-Xanthocidin using FeCl3-Mediated Nazarov Reaction, Tetrahedron, 66, 9808-9813, 2010.12.
45. Kazumasa Matsuo, Mitsuru Shindo, Cu(II)-Catalyzed Acylation by Thiol Esters Under Neutral Conditions: Tandem Acylation-Wittig Reaction Leading to a One-Pot Synthesis of Butenolides, Organic letters, 12, 5346-5349, 2010.11.
46. Kazumasa Matsuo, Keiko Ohtsuki, Takashi Yoshikawa, Kozo Shishido, Kaori Yokotani-Tomita, Mitsuru Shindo, Total Synthesis of Xanthanolides, Tetrahedron, 10.1016/j.tet.2010.08.061, 66, 8407-8419, 2010.09.
47. Kentaro Yaji, Mitsuru Shindo, Construction of a fully substituted cyclopentenone as the core skeleton of stemonamide via a Nazarov cyclization, Tetrahedron Letters, 10.1016/j.tetlet.2010.08.032, 51, 5469-5472, 2010.08.
48. 吉川孝, 新藤充, Stereoselective Synthesis of (E)-2-en-4-ynoic acids with Ynolates. Catalytic Conversion to Tetronic acids and 2-Pyrones, Organic letters, 11, 23, 5378-5381, 2009.11.
49. T. Yosikawa, S. Mori, M. Shindo , The Effects of C-S and C-Se bonds on torquoselectivity: stereoselective olefination of alpha-thio- and alpha-selenoketones with ynolates, Tetrahedron,, 65, 8832-8838 , 2009.10.
50. K. Yaji, M. Shindo,, Chiral Acid-Catalyzed Asymmetric Nazarov Reaction. Nucleophilic Construction of a Quaternary Asymmetric Center at the a-Position of the Keto Function, Synlett, 2524-2528, 2009.08.
51. 佐藤幸子, 麻生祥文, 新藤充, Efficient synthesis of bongkrekic acid. Three component convergent strategy, Tetrahedron Lett., 50 , 4164-4166, 2009.06.
52. M. Shindo,Y. Yamamoto, K. Yamada, K. Tomioka, Asymmetric construction of binaphthyl by the chiral diether-mediated conjugate addition of naphthyllithium to naphthalenecarboxylic acid BHA ester, Chem. Pharm. Bull., 57, 752-754, 2009.05.
53. T. Yoshikawa, S. Mori, M. Shindo, The Effect of Alkynyl Groups on Torquoselectivity. Highly Stereoselective Olefination of Alkynyl Ketones with Ynolates, Journal of the American Chemical Society, 131, 2092–2093, 2009.01.
54. Kazumasa Matsuo, Hiromasa Yokoe, Kozo Shishido, Mitsuru Shindo, Synthesis of Diversifolide and Structure Revision, Tetrahedron Lett., 49, 4279-4281, 2008.05.
55. K. Ohtsuki, K. Matsuo, T. Yoshikawa, C. Moriya, K. Yokotani, K. Shishido, M. Shindo, Total Synthesis of (+) and (-)-Sundiversifolide and Determination of the Absolute Cnfiguration, Organic Letters, 10, 1247-1250, 2008.04.
56. M. Shindo, Y. Yoshimura, M. Hayashi, H. SOejima, T. Yoshikawa, K. Matsumoto, K. Shishido, Synthesis of Multisubstituted Furans, Pyrroles, and Thioophenes via Ynolates, Organic Letters, 9, 1963-1966, 2007.05.
57. Mitsuru Shindo, Kentaro Yaji, Taisuke Kita, Kozo Shishido, Acid-Catalyzed Nazarov Reaction Controlled by -Alkoxy Groups, Synlett, 1096, 2007.04.
58. Mitsuru Shindo, Kenji Matsumoto, Kozo Shishido,, Hyperconjugative Effect of C-Ge Bonds: Synthesis of Multisubstituted Alkenylgermanes via Torquoselective Olefination of Acylgermanes with Ynolates, Tetrahedron, 63, 4271-4277, 2007.04.
59. Mitsuru Shindo, Kenji Matsumoto, Kozo Shishido, Generation of Ynolate and Z-Selective Olefination of Acylsilanes: (Z)-2-Methyl-3-Trimethylsilyl-2-butenoic acid, Organic Synthesis, 84, 11-21, 2007.01.
60. Mitsuru Shindo,*† Taisuke Kita, Toshihiro Kumagai, Kenji Matsumoto, Kozo Shishido, Synthesis of Tetrasubstituted and Functionalized Enol Ethers by E-Selective Olefination of Esters with Ynolates, J. Am. Chem. Soc., 128, 1062-1063, 2006.01.
61. Mitsuru Shindo,* Takashi Yoshikawa, Yasuaki Itou, Seiji Mori, Takeshi Nishii, Kozo Shishido, Heteroatom-Guided Torquoselective Olefination of alpha-Oxy and alpha-Amino Ketones via Ynolates, Chemistry-Europian Journal, 10.1002/chem.200500574, 12, 2, 524-536, 2005.10.
62. Mitsuru Shindo,* Keiko Ohtsuki, Kozo Shishido,, Asymmetric inverse electron-demand 1,3-dipolar cycloaddition of ynolates with a chiral nitrone derived from L-serine leading to beta-amino acid derivatives,, Tetrahedron: Asymmetry,, 10.1016/j.tetasy.2005.07.023, 16, 16, 2821-2831, 2005.07.
63. Mitsuru Shindo, Kenji Matsumoto and Kozo Shishido, A synthesis of multisubstituted vinylsilanes via ynolates: stereoselective formation of -silyl--lactones followed by decarboxylation, Chem. Commun., 2477, 2005.05.
64. M. Shindo, K. Matsumoto, K. Shishido, Intramolecularly Activated Vinylsilanes: Fluoride-free Cross-Coupling of (Z)-β-(Trialkylsilyl)acrylic Acids, Synlett, 176-178, 2005.01.
65. T. Yoshimura, T. Bando, M. Shindo, K. Shishido,, Diastereoselective Synthesis of the 19-epi-C18-C25 Segment of (+)-Lasonolide A and an Unusual Inversion at C19,, Tetrahedron Letters,, 45, 9241-9244, 2004.10.
66. Mitsuru Shindo,* Tomoyuki Sugioka, Kozo Shishido,, Electronic effect on the regioselectivity in the ring opening of para-substituted phenyloxiranes by acetylides,, Tetrahedron Lett., 45, 9265-9268, 2004.10.
67. S. Mori, M. Shindo,, Hyperconjugative Effects in the Stereoselective Ring Opening Reactions of Oxetenoxides, Org. Lett., 22, 3945-3948, 2004.06.
68. Y. Fukuda, M. Shindo, K. Shishido,, A formal total synthesis of (-)-limaspermine,, Heterocycles, 62, 787-792, 2004.02.
69. M. Shindo, Y. Sato, T. Yoshikawa, R. Koretsune, K. Shishido,, Stereoselective Olefination of Unfunctionalized Ketones via Ynolates, J. Org. Chem, 69, 3912-3916, 2004.01.
70. M. Shindo, Y. Sato, R. Koretsune, T. Yoshikawa, K. Matsumoto, K. Itoh, K. Shishido,, Synthesis of -Dibromo Esters as Precursors of Ynolates, Chem. Pharm. Bull.,, 51, 477-478, 2003.02.
71. M. Shindo. K. Itoh, K. Ohtsuki, C. Tsuchiya, K. Shishido,, Diastereoselective 1,3-Dipolar Cycloaddition of Ynolates with Chiral Nitrones, Synthesis, 1441-1445, 2003.01.
1. Mitsuru Shindo, Generation and reactions of lithium ynolates: Regioselective one-pot synthesis of triptycenes, Pacifichem2021, 2021.12.
2. Mitsuru Shindo, Takayuki Iwata, Arihiro Kano, Yoshiharu Fujii,, Studies on Plant Root Gravitropism Inhibitors Derived from Allelochemical,, The 1st International Symposium on Chemical Communication (ISCC2019),, 2019.01.
3. #Furusawa、Y., #, Sun, J., Iwata, T., Shindo, M.,, Synthesis of Molecular Probes of Cis-Cinnamic Acid Analog with Antigravitropic Activity, 4th International Conference of Asian Allelopathy Society, 2018.09, アレロパシー活性化合物の分子イメージング実験から得られた結果を元に、新規植物重力屈性阻害化合物の開発に成功し、さらにその分子蛍光プローブを合成し、その分子イメージング実験により局在部位に関する情報を得た。.
4. M. Shindo, Regioselective One-pot Synthesis of Triptycenes via Triple Cycloaddition of Arynes to Ynolates,, The 12th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-12), 2017.11.
5. 新藤 充, 和宇慶久, 松尾和真, 松本 健司, Cu(II)-catalyzed Dissymmetrization of Dithiomalonates, Pacifichem2015, 2015.12.
6. 松本 健司, 堂籠 健斗, 新藤 充, Heterogeneous Rh-catalyzed Oxidative Coupling of Arylamines, XXVI International Conference on Organometallic Chemistry, ICOMC2014, 2014.07.
7. 新藤 充, Total Synthesis of Stemonamine, ISIS-8, 2013.11.
8. 新藤 充, Reactions of Ynolates and Synthetic Applications, 10th International Symposium on Carbanion Chemistry, 2013.09, イノラートの生成と合成的応用について講演した.
9. 新藤 充, Olefination Controlled by Torquoselectivity, Nang Young Technological University organic chemistry symposium, 2013.01.
10. 新藤 充, Total Synthesis of Stemonamine, Cambodian Maleysian Chemical Congress, 2012.10.
11. 新藤 充, 寺井やすあき, 行平大地, 三浦 大典, 藤村 由紀, 松本 健司, 割石 博之, Design and synthesis of new efficient MALDI-MS matrices for low molecular weight metabolites in negative ionization mode, 19th International Mass Specrometry Conference (IMSC2012, 2012.09.
12. Catalytic Nazarov Reaction.
13. Torquoselective Olefination.
14. One-pot synthesis of multisubstituted furans via ynolates,.
15. The Coupling reaction of trialkylvinylsilanes and vinylgermanes using activation by hypervalency.
16. Synthetic Study of Sundiversifolide.
Educational Activities
Organic synthetic chemistry is very important for supplying useful organic compounds such as medical drugs and materials. If carbon reactive species, which might be regarded as classical chemistry, have high functionality, they can work as non-classical reactive species. I am continuing to develop novel multi-functional reactive species, for examples, ynolates and ester dianions.