Faculty Profiles - IWATA TAKAYUKI

Information

写真a

IWATA TAKAYUKI

Organization

Institute for Materials Chemistry and Engineering Department of Fundamental Organic Chemistry Assistant Professor
Interdisciplinary Graduate School of Engineering Sciences Department of Interdisciplinary Engineering Sciences（Joint Appointment）

Contact information

Tel

0925837805

Profile

My research is focused on 1) development of new organic reactions, 2) synthesis of biological active compounds and 3) synthesis of new aromatic compounds based on triptycenes.

Homepage

https://shindo-kano-lab.weebly.com/

External link

Degree

Ph. D.

Research History

Kyushu University Institute for Materials Chemistry and Engineering Assistant Professor

2016.4 - Present

Research Interests・Research Keywords

Research theme：My research involves 1) development of novel organic reactions, 2) synthesis of biological active compounds including natural products and 3) synthesis of functional molecules based on triptycenes.

Keyword：organic synthesis, new reaction development, triptycene

Research period： 2016.4

Awards

日本薬学会九州山口支部学術奨励賞

2024.11 日本薬学会九州山口支部生体分子機能の制御に向けた機能性分子の合成

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Award type：Award from international society, conference, symposium, etc.
有機合成化学協会九州山口支部優秀論文賞

2022.6 有機合成化学協会九州山口支部 Quadruple Role of Pd Catalyst in Domino Reaction Involving Aryl to Alkyl 1,5-Pd Migration to Access 1,9-Bridged Triptycenes

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日本化学会第101回春季年会　若い世代の特別講演会証

2021.3 日本化学会
2017年有機合成化学協会味の素研究企画賞

2018.2 有機合成化学協会

Papers

A Strategy Based on “Ambident Anthracene” for the Synthesis of Higher-Order Iptycenes Invited Reviewed International journal

30 ( 9 ) e202303687 2023.11

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

An efficient method for the synthesis of higher-order iptycenes using an “ambident anthracene” building block is presented. For that purpose, an iterative elongation strategy involving the ring-opening of an endoxide to give a highly reactive anthranoxide, followed by a Diels-Alder reaction with an aryne was used. The method systematically provides higher-order iptycenes, including trideciptycene, which is the longest-chain iptycene synthesized so far.

DOI： doi.org/10.1002/chem.202303687
3-Trifluoromethylbenzyne: Precise Orientation in Cycloaddition Reaction Enabled Regioselective Synthesis of Trifluoromethylated Triptycenes Reviewed International journal

Synthesis 2022.4

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Language：English Publishing type：Research paper (scientific journal)
Retro-Friedel-Crafts-Type Acidic Ring-Opening of Triptycenes: A New Synthetic Approach to Acenes Reviewed International journal

T. Iwata, R. Kawano, T. Fukami, M. Shindo

Chem. Euro. J. 28 ( 12 ) e202104160 2022.1 （ ISSN:0947-6539 eISSN:1521-3765 ）

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

DOI： 10.1002/chem.202104160

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PubMed
Cycloaddition Initiated by Ynolates: High-Energy Dianion Equivalents as a Molecular Glue Reviewed International journal

Synlett 33 ( 06 ) 531 - 545 2021.11 （ ISSN:0936-5214 eISSN:1437-2096 ）

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

DOI： 10.1055/s-0040-1719857

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Scopus
Quadruple Role of Pd Catalyst in Domino Reaction Involving Aryl to Alkyl 1,5-Pd Migration to Access 1,9-Bridged Triptycenes. Reviewed International journal

T. Iwata, S. Kumagai, T. Yoshinaga, M. Hanada, Y. Shiota, K. Yoshizawa, M. Shindo

Chem. Euro. J. accepted 2021.6

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Language：English Publishing type：Research paper (scientific journal)
Flow synthesis of triptycene via triple cycloaddition of ynolate to benzyne Invited Reviewed International journal

T. Iwata, T. Yoshinaga, M. Shindo

2020.7

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Language：English Publishing type：Research paper (scientific journal)
Anthranoxides as Highly Reactive Arynophiles for Synthesis of Triptycenes Invited Reviewed International journal

Takayuki Iwata, Mizuki Hyodo, Takuto Fukami, Yoshihito Shiota, Kazunari Yoshizawa, Mitsuru Shindo

Chem. Euro. J. 26, 8506-8510 (2020). 2020.5

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Language：Japanese Publishing type：Research paper (scientific journal)
Synthesis of Distorted 1,8,13-Trisilyl-9-hydroxytriptycenes by Triple Cycloaddition of Ynolates to 3-Silylbenzynes Invited Reviewed International journal

T. Yoshinaga, T. Fujiwara, T. Iwata, and M. Shindo

Chem. Eur, J. 25, 13855 (2019) 25 13855 2019.7

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Language：Japanese Publishing type：Research paper (scientific journal)
Regioselective One-pot Synthesis of Triptycenes via Triple-Cycloadditions of Arynes to Ynolates

S. Umezu, G. d. P. Gomes, T. Yoshinaga, M.Sakae, K. Matsumoto, T. Iwata, I. Alabugin, M. Shindo

Angew. Chem. Int. Ed. 56, 1298-1302 (2017) 2016.12

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Language：English
Practical Synthesis of α,α-Dibromo Esters from Aldehydes

Iwata, T; Hatae, K; Shindo, M

JOURNAL OF ORGANIC CHEMISTRY 89 ( 14 ) 10384 - 10387 2024.7 （ ISSN:0022-3263 eISSN:1520-6904 ）

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Language：English Publisher：Journal of Organic Chemistry

Herein, we report an efficient and practical method for synthesizing α,α-dibromo esters, which are the precursors of ynolates, through the dibromination of aldehydes followed by oxidative esterification using iodine. Our method was successfully employed in a large-scale synthesis to yield more than 30 g of dibromo esters. These two steps can be performed in a one-pot manner, which makes the method adaptable even for aldehydes having low boiling points.

DOI： 10.1021/acs.joc.4c01078

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PubMed
Nazarov reaction triggered by active lithium salts in cyclopentyl methyl ether

Iwata, T; Funatsu, S; Shindo, M

CHEMISTRY LETTERS 53 ( 3 ) 2024.3 （ ISSN:0366-7022 eISSN:1348-0715 ）

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Publisher：Chemistry Letters

In this study, we developed a lithium-activated Nazarov reaction of highly activated divinyl ketones in the presence of mixed lithium salts by combining LiClO4 with either LiOMe or LiI in cyclopentyl methyl ether (CPME). This reaction produces LiOPh in the reaction mixture, exhibiting aspects of a Nazarov reaction in the presence of base. The additives LiOMe and LiI not only facilitated the dissolution of LiClO4 aggregates but also promoted the addition–elimination mechanism, thereby accelerating the reaction and preventing side reactions.

DOI： 10.1093/chemle/upad046

Web of Science

Scopus
A Strategy Based on "Ambident Anthracene" for the Synthesis of Higher-Order Iptycenes

Iwata, T; Hyodo, M; Kawano, R; Shindo, M

CHEMISTRY-A EUROPEAN JOURNAL 30 ( 9 ) e202400145 2024.2 （ ISSN:0947-6539 eISSN:1521-3765 ）

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

Invited for the cover of this issue is the group of Takayuki Iwata and Mitsuru Shindo at Kyushu University. The image depicts the longest-chain iptycene synthesized in this study, showing the connections between iptycene synthetic units by using transparent cases. Read the full text of the article at 10.1002/chem.202303687.

DOI： 10.1002/chem.202400145

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PubMed
Front Cover: A Strategy Based on “Ambident Anthracene” for the Synthesis of Higher‐Order Iptycenes (Chem. Eur. J. 9/2024)

Chemistry – A European Journal 2024.2

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DOI： 10.1002/chem.202400144
Neutral Nazarov reaction using protic solvents as activators

Iwata, T; Funatsu, S; Kajiwara, K; Shiota, Y; Yoshizawa, K; Shindo, M

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 97 ( 2 ) 2024.2 （ ISSN:0009-2673 eISSN:1348-0634 ）

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Publisher：Bulletin of the Chemical Society of Japan

Herein, we report a neutral Nazarov reaction using protic solvents instead of strong acids as activators. The key to the success of this reaction lies in the rational design of the divinyl ketone substrates. In particular, the introduction of electron-donating groups (EDGs) at the β- and β′-positions of the carbonyl group in the divinyl ketone increases the Lewis basicity dramatically, an EDG at α-position promotes the cyclization, and the presence of a phenoxy group at β-position enables the irreversible elimination of phenol from the cyclized intermediate, thus shifting the reversible cyclization to the product side. This phenol-releasing reaction can be applied to clip chemistry to target acidic biological environments.

DOI： 10.1093/bulcsj/uoad014

Web of Science

Scopus
A Strategy Based on "Ambident Anthracene" for the Synthesis of Higher-Order Iptycenes

Iwata, T; Hyodo, M; Kawano, R; Shindo, M

CHEMISTRY-A EUROPEAN JOURNAL 30 ( 9 ) e202303687 2023.12 （ ISSN:0947-6539 eISSN:1521-3765 ）

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Language：English Publisher：Chemistry - A European Journal

An efficient method for the synthesis of higher-order iptycenes using an “ambident anthracene” building block is presented. For that purpose, an iterative elongation strategy involving the ring-opening of an endoxide to give a highly reactive anthranoxide, followed by a Diels-Alder reaction with an aryne was used. The method systematically provides higher-order iptycenes, including trideciptycene, which is currently the iptycene with the longest chain to have been synthesized. X-ray crystallography revealed interesting structures in which solvent molecules fill the cavities of these iptycenes, thus creating a “honeycomb” structure with the solvent molecules arranged in tubular spaces.

DOI： 10.1002/chem.202303687

Web of Science

Scopus

PubMed
Nazarov reaction triggered by active lithium salts in cyclopentyl methyl ether Reviewed International journal

T. Iwata, S. Funatsu, M. Shindo

Chem. Lett. 53 ( 3 ) upad046 2023.12

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

DOI： doi.org/10.1093/chemle/upad046
Neutral Nazarov reaction using protic solvents as activators Reviewed International journal

T. Iwata, S. Funatsu, K. Kajiwara, Y. Shiota, K. Yoshizawa, M. Shindo

Bull. Chem. Soc. Jpn. 97 ( 2 ) uoad014 2023.12

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

DOI： doi.org/10.1093/bulcsj/uoad014
Intramolecular Hiyama Coupling: Synthesis of 1,8,13-Trisubstituted Chiral Triptycenes with Three Different Substituents by Intramolecular Substituent Transfer

Iwata, T; Hanada, M; Kumagai, S; Yoshinaga, T; Shiota, Y; Yoshizawa, K; Shindo, M

CHEMISTRY-A EUROPEAN JOURNAL 29 ( 39 ) e202300988 2023.7 （ ISSN:0947-6539 eISSN:1521-3765 ）

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Language：English Publisher：Chemistry - A European Journal

Herein, we describe Hiyama coupling via intramolecular substituent transfer from silicon on one blade of triptycenes to another to yield 1,8,13-trisubstituted chiral triptycenes. This reaction is attributed to the proximity effect of substituents on triptycene, which plays an important role in not only the formation of the oxy-palladacycle but also the activation of the silyl group to facilitate σ-bond metathesis. After bromination and nucleophilic ring opening, the second intramolecular Hiyama coupling provided various 1,8,13-trisubstituted chiral triptycenes. The optical resolution of 1,8,13-triptycene afforded an optically active form for the first time.

DOI： 10.1002/chem.202300988

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Cover Feature: Intramolecular Hiyama Coupling: Synthesis of 1,8,13‐Trisubstituted Chiral Triptycenes with Three Different Substituents by Intramolecular Substituent Transfer (Chem. Eur. J. 39/2023)

Chemistry – A European Journal 2023.7

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DOI： 10.1002/chem.202301655
Design and synthesis of strong root gravitropism inhibitors with no concomitant growth inhibition Reviewed International journal

T. Nishimura, S. Makigawa, J. Sun, K. Kodama, H. Sugiyama, K. Matsumoto, T. Iwata, N. Wasano, A. Kano, M. Terao Morita, Y. Fujii & M. Shindo

Sci. Rep. 13 5173 2023.6

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Language：English Publishing type：Research paper (scientific journal)
Intramolecular Hiyama Coupling: Synthesis of 1,8,13-Trisubstituted Chiral Triptycenes with Three Different Substituents by Intramolecular Substituent Transfer Reviewed International journal

T. Iwata, M. Hanada, S. Kumagai, T. Yoshinaga, Y. Shiota, K. Yoshizawa, M. Shindo

Chem. Eur. J. 29 ( 39 ) e202300988 2023.4

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

DOI： doi.org/10.1002/chem.202300988
Design and synthesis of strong root gravitropism inhibitors with no concomitant growth inhibition

Nishimura, T; Makigawa, S; Sun, J; Kodama, K; Sugiyama, H; Matsumoto, K; Iwata, T; Wasano, N; Kano, A; Morita, MT; Fujii, Y; Shindo, M

SCIENTIFIC REPORTS 13 ( 1 ) 5173 2023.3 （ ISSN:2045-2322 ）

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Language：English Publisher：Scientific Reports

Herein, we describe a highly potent gravitropic bending inhibitor with no concomitant growth inhibition. Previously, we reported that (2Z,4E)-5-phenylpenta-2,4-dienoic acid (ku-76) selectively inhibits root gravitropic bending of lettuce radicles at 5 μM. Based on the structure–activity relationship study of ku-76 as a lead compound, we designed and synthesized various C4-substituted analogs of ku-76. Among the analogs, 4-phenylethynyl analog exhibited the highest potency for gravitropic bending inhibition, which was effective at only 0.01 μM. Remarkably, 4-phenylethynyl analog is much more potent than the known inhibitor, NPA. Substitution in the para position on the aromatic ring of 4-phenylethynyl group was tolerated without diminished activity. In addition, evaluation using Arabidopsis indicated that 4-phenylethynyl analog inhibits gravitropism by affecting auxin distribution in the root tips. Based on the effects on Arabidopsis phenotypes, 4-phenylethynyl analog may be a novel inhibitor that differs in action from the previously reported auxin transport inhibitors.

DOI： 10.1038/s41598-023-32063-z

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Synthesis and Conversion of Bongkrekic Acid and its Bioactivity

Shindo Mitsuru, Iwata Takayuki, Kano Arihiro, Shinohara Yasuo

Journal of Synthetic Organic Chemistry, Japan 80 ( 12 ) 1136 - 1148 2022.12 （ ISSN:00379980 eISSN:18836526 ）

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

Bongkrekic acid (BKA), isolated from the bacterium Burkholderia gladioli, is an inhibitor of adenine nucleotide translocator in the mitochondria inner membrane, and is also a suppressor of apoptosis. Therefore, BKA is an important tool for the investigation of apoptosis as well as mitochondria. Herein, we summarize our total synthesis of BKA and its analogues, and their biological activities. The total synthesis was achieved by employing a three-component convergent strategy based on Julia-Kocienski olefination and Suzuki coupling. Torquoselective olefination with an ynolate was applied for the efficient construction of an unsaturated ester. Based on the total synthesis, various BKA analogues were prepared for structure-activity relationship studies, which indicated that the carboxylic acid moieties were essential for the biological activities of BKA. More readily available BKA analogues with potent biological activity were also developed. A brief summary of the novel biological activities is also provided.

DOI： 10.5059/yukigoseikyokaishi.80.1136

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CiNii Research
Genetic variants associated with glaucomatous visual field loss in primary open-angle glaucoma

Mabuchi, F; Mabuchi, N; Sakurada, Y; Yoneyama, S; Kashiwagi, K; Yamagata, Z; Takamoto, M; Aihara, M; Iwata, T; Hashimoto, K; Sato, K; Shiga, Y; Nakazawa, T; Akiyama, M; Kawase, K; Ozaki, M; Araie, M

SCIENTIFIC REPORTS 12 ( 1 ) 20744 2022.12 （ ISSN:2045-2322 ）

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Language：English

DOI： 10.1038/s41598-022-24915-x

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Efficacy of empagliflozin in heart failure with preserved versus mid-range ejection fraction: a pre-specified analysis of EMPEROR-Preserved

Anker, SD; Butler, J; Usman, MS; Filippatos, G; Ferreira, JP; Bocchi, E; Böhm, M; Brunner-La Rocca, HP; Choi, DJ; Chopra, V; Chuquiure, E; Giannetti, N; Gomez-Mesa, JE; Janssens, S; Januzzi, JL; González-Juanatey, JR; Merkely, B; Nicholls, SJ; Perrone, SV; Piña, IL; Ponikowski, P; Senni, M; Sim, D; Spinar, J; Squire, I; Taddei, S; Tsutsui, H; Verma, S; Vinereanu, D; Zhang, J; Iwata, T; Schnee, JM; Brueckmann, M; Pocock, SJ; Zannad, F

NATURE MEDICINE 28 ( 12 ) 2512 - + 2022.12 （ ISSN:1078-8956 eISSN:1546-170X ）

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Language：English

DOI： 10.1038/s41591-022-02041-5

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3-Trifluoromethylbenzyne: Precise Orientation in Cycloaddition Reaction Enabled Regioselective Synthesis of Trifluoromethylated Triptycenes

Iwata, T; Hyodo, M; Fujiwara, T; Kawano, R; Kuhn, L; Alabugin, IV; Shindo, M

SYNTHESIS-STUTTGART 54 ( 22 ) 4971 - 4978 2022.11 （ ISSN:0039-7881 eISSN:1437-210X ）

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Publisher：Synthesis (Germany)

The first regioselective addition reactions to 3-trifluoromethylbenzyne are reported. Triple cycloaddition of ynolates to the benzyne provided 1,8,13-tris(trifluoromethyl)triptycenes with high regioselectivity. 1-Trifluoromethyltriptycenes were regioselectively obtained by the Diels-Alder reaction of anthranoxides with the benzyne. These selectivities are attributed to the electron-acceptor nature of the trifluoromethyl group on the benzyne.

DOI： 10.1055/a-1818-0576

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Retro-Friedel-Crafts-Type Acidic Ring-Opening of Triptycenes: A New Synthetic Approach to Acenes

Iwata T., Kawano R., Fukami T., Shindo M.

Chemistry (Weinheim an der Bergstrasse, Germany) 28 ( 12 ) e202200416 2022.2 （ ISSN:0947-6539 ）

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

Invited for the cover of this issue is the group of Takayuki Iwata, Mitsuru Shindo, and co-workers at Kyushu University. The image depicts ring-opening of triptycenes to afford corresponding anthrones by acid treatment. Read the full text of the article at 10.1002/chem.202104160.

DOI： 10.1002/chem.202200416

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PubMed
Front Cover: Retro‐Friedel‐Crafts‐Type Acidic Ring‐Opening of Triptycenes: A New Synthetic Approach to Acenes (Chem. Eur. J. 12/2022)

Chemistry – A European Journal 2022.2

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DOI： 10.1002/chem.202200415
Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity Reviewed International journal

M. Shindo, S. Makigawa, K. Kodama, H. Sugiyama, K. Matsumoto, T. Iwata, N. Wasano, A. Kano, M. T. Morita, Y. Fujii

Phytochemistry 179, 112508 (2020). 2020.6

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Language：English Publishing type：Research paper (scientific journal)
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 Invited Reviewed International journal

Jun Sun, Takayuki Iwata, Mitsuru Shindo

Chem. Lett. 49, 1084 (2020). 2020.6

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Language：English Publishing type：Research paper (scientific journal)
(–)-Isostemonamine can enhance the anti-proliferative activity of trichostatin A against human breast cancer MDA-MB-231 cells Invited Reviewed International journal

2020.1

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Language：Japanese Publishing type：Research paper (scientific journal)
Mild Environment-Friendly Oxidative Debenzylation of N-Benzylanilines using DMSO as an Oxidant Invited Reviewed International journal

Tatsuro Yoshinaga, Takayuki Iwata, Mitsuru Shindo

Chem Lett 49, 191-194 (2020) 2020.1

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Language：Japanese Publishing type：Research paper (scientific journal)
Essential structural features of (2Z,4E)-5-phenylpenta-2,4-dienoic acid for inhibition of root gravitropism Reviewed International journal

Mitsuru Shindo, Saki Makigawa, Kenji Matsumoto, Takayuki Iwata, Naoya Wasano, Arihiro Kano, Miyo Terao Morita, Yoshiharu Fujii

Phytochemistry 172, 112287 (2020) 2020.1

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Language：Japanese Publishing type：Research paper (scientific journal)
Synthesis of Ynolates via Double Deprotonation of Non-Brominated Esters Invited Reviewed International journal

J. Sun, T. Yoshiiwa, T. Iwata, M. Shindo

Org. Lett. 21, 6585 (2019) 2019.6

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Language：Japanese Publishing type：Research paper (scientific journal)
Anti-proliferative effects of (–) -isostemonamine on highly aggressive human breast cancer MDA-MB-231 cells Invited Reviewed International journal

2018.11

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Language：Japanese Publishing type：Research paper (scientific journal)
First Asymmetric Total Synthesis of (-)-Isostemonamine and Kinetic Analysis of its Isomerizations International journal

T. Iwata, T. Tomiyama, S. Fujita, and M. Shindo

2018.3

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Language：English Publishing type：Research paper (scientific journal)
Synthesis and evaluation of simplified functionalized bongkrekic acid analogs

S. Fujita, M. Suyama, K. Matsumoto, A. Yamamoto, T. Yamamoto, Y. Hiroshima, T. Iwata, A. Kano, Y. Shinohara, and M. Shindo

Tetrahedron 74, 962-969 (2018) 2018.1

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Language：English
Asymmetric Total Synthesis of (-)-Stemonamine and its Stereochemical Stability

S. Fujita, K. Nishikawa, T. Iwata, T. Tomiyama, H. Ikenaga, K. Matsumoto, M. Shindo

Chem. Eur. J. 24, 1539-1543 (2018) 2017.12

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Language：English
Aerobic Oxidative Homocoupling Reaction of Anilides Using Heterogeneous Metal Catalysts

S. Fujimoto, K. Matsumoto, T. Iwata, M. Shindo

Tetrahedron Lett. 58,973-976(2017) 2017.1

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Presentations

3-トリフルオロメチルベンザインを用いたトリプチセンの合成

岩田隆幸、藤原匠、兵頭瑞樹、川野隆生、Leah Kuhn、Igor Alabugin、新藤充

日本化学会第102春季年会 (2022) 2022.3

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Event date： 2022.3

Language：Japanese Presentation type：Oral presentation (general)

Venue：オンライン Country：Japan
Regioselective synthesis of 1,8,13-syn-substituted triptycenes using triple cycloaddition of ynolates to 3-silylbenzynes International conference

Takayuki Iwata, Tatsuro Yoshinaga, Yusuke Maehata, Takumi Fujiwara, Mitsuru Shindo

Pacifichem 2021 2021.12

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Event date： 2021.12

Language：English Presentation type：Oral presentation (general)

Country：United States
1,5-Pd移動を鍵としたトリプチセンの連続的還元-環化-鈴木カップリング反応

岩田隆幸, 熊谷智, 吉永達郎, 塩田淑仁, 吉澤一成, 新藤充

日本薬学会第141年会 2021.3

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Event date： 2021.3

Language：Japanese Presentation type：Oral presentation (general)

Venue：オンライン Country：Japan
syn 置換トリプチセンを基盤とした分子空間の創出 Invited

岩田隆幸

日本化学会第101春季年会 (2021) 2021.3

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Event date： 2021.3

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

Venue：オンライン Country：Japan

トリプチセンは3つのベンゼン環が縮環したプロペラ型分子である。本分子の1,8,13位は橋頭位9位とともに同一平面上に存在し、これら位置の置換基は、この平面に垂直かつ互いに等間隔に位置することで、その間に分子空間を作る。本研究では、発表者らが最近見出したイラノートとベンザインの3連続環化付加反応1を利用したsyn(1,8,9,13)置換トリプチセンの合成と、それを基盤とした分子空間の創出について検討した。
イノラートに対して、種々の置換ベンザイン2を作用させた結果、3-メトキシおよび3-シリルベンザインを用いると、位置選択的にsyn置換トリプチセンが得られることを見出した。さらに、シリル基を足掛かりとした変換反応により、内部に分子空間を有するカゴ型トリプチセン、および、環状構造をもつトリプチセンの合成に成功した。また、キラルな分子空間をもつトリプチセンの合成にも成功したので、あわせて紹介する。
1,5-パラジウム移動を経由する1,9-架橋トリプチセンの合成

岩田隆幸、熊谷智、吉永達郎、新藤充

第117回有機合成シンポジウム 2021.10

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Event date： 2020.10

Language：Japanese Presentation type：Oral presentation (general)

Venue：オンライン Country：Japan
ジビニルケトンのLewis塩基性向上を鍵とした弱酸応答性ナザロフ反応の開発

岩田隆幸、梶原康平、船津心吾、新藤充

日本薬学会第140年会 2020.3

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Event date： 2020.6

Language：Japanese

Country：Japan
イノラート・アライン３連続環化付加反応を基盤とした高官能基化トリプチセンアラインの生成

岩田　隆幸・深見　拓人・新藤　充

日本化学会第100春季年会 (2020) 2020.3

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Event date： 2020.6

Language：Japanese

Country：Japan
β-アルコキシジビニルケトンを基本骨格とした弱酸応答性ナザロフ反応の開発

岩田隆幸・梶原康平・船津心吾・新藤充

第116回有機合成シンポジウム 2019.10

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Event date： 2020.2

Language：Japanese

Country：Japan
ステモナアルカロイドの不斉全合成とその異性化解析

岩田隆幸，藤田聡，富山泰至，松本健司，新藤充

第44回反応と合成の進歩シンポジウム 2018.10

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Event date： 2020.2

Language：Japanese

Country：Japan
Regioselective Synthesis of Substituted Triptycenes Using Ynolate-aryne Triplecycloadditions International conference

Takayuki Iwata, Tatusro Yoshinaga, Satoshi Umezu, Takumi Fujiwara,Mikei Sakae, Kenji Matsumoto, Mitsuru Shindo

IKCOC-14 2018.11

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Event date： 2020.2

Language：English

Country：Japan
Asymmetric Total Synthesis, Stereochemical Stability and Cancer Cell Killing Effects of Stemona Alkaloids

Takayuki Iwata, Satoshi Fujita, Taishi Tomiyama, Kenji Matsumoto, Masayo Hirao-Suzuki, Shuzo Takeda, Mitsuru Shindo

The 99th CSJ Annual Meeting 2019.3

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Event date： 2020.2

Language：English

Country：Japan
シス桂皮酸を起点とした植物根に対する重力屈性阻害剤の開発

岩田隆幸, 古澤佑貴, 牧川早希, 福田洋, 児玉梢, 和佐野直也, 福永幸裕, 奥田勝博, 孫軍, 西川慶祐, 河本ひとみ, 松本健司, 狩野有宏, 森田(寺尾) 美代, 藤井義晴, 新藤充

第61回天然有機化合物討論会 2019.9

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Event date： 2020.2

Language：Japanese

Country：Japan
イノラート・アライン３連続環化付加反応を用いた歪みトリプチセンおよびイプチセンの合成

岩田隆幸・吉永達郎・深見拓人・藤原匠・新藤充

第30回基礎有機化学討論会 2019.9

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Event date： 2020.2

Language：Japanese

Country：Japan
トリプチセン型ホスフィン配位子Trip-phosの合成とその評価

波多江貴一、花田将人、岩田隆幸、新藤充

日本薬学会第144年会 2024.3

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Event date： 2024.3

Language：Japanese

Venue：パシフィコ横浜 Country：Japan
活性リチウム塩触媒による“塩基性”ナザロフ反応

船津心吾、岩田隆幸、新藤充

日本薬学会第144年会 2024.3

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Event date： 2024.3

Language：Japanese

Venue：パシフィコ横浜 Country：Japan
天然物を基盤とした新規ビナミジニウム型 UV-A 吸収剤の開発

岩田愛紗、岩田隆幸、新藤充

日本薬学会第144年会 2024.3

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Event date： 2024.3

Language：Japanese

Venue：パシフィコ横浜 Country：Japan
ベンザインとシリルイノールエーテルとの環化付加反応によるベンゾフランの合成

賀來武志、岩田隆幸、新藤充

日本化学会第104春季年会 (2024) 2023.3

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Event date： 2024.3

Language：Japanese

Venue：日本大学理工学部船橋キャンパス Country：Japan
脂質ミミックとなるトリプチセンの合成と機能

東恩納一樹、岩田隆幸、木下祥尚、松森信明、新藤充

日本化学会第104春季年会 (2024) 2023.3

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Event date： 2024.3

Language：Japanese

Venue：日本大学理工学部船橋キャンパス Country：Japan
シクロドデシプチセンの合成

兵頭瑞樹、岩田隆幸、新藤充

日本化学会第104春季年会 (2024) 2023.3

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Event date： 2024.3

Language：Japanese

Venue：日本大学理工学部船橋キャンパス Country：Japan
脂質ミミックトリプチセンの合成と評価

東恩納一樹、岩田隆幸、木下祥尚、松森信明、新藤充

第40回日本薬学会九州山口支部大会 2023.11

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Event date： 2023.11

Language：Japanese

Venue：第一薬科大学薬学部 Country：Japan
トリプチセン型ホスフィン配位子の合成と評価

波多江貴一、花田将人、岩田隆幸、新藤充

第40回日本薬学会九州山口支部大会 2023.11

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Event date： 2023.11

Language：Japanese

Venue：第一薬科大学薬学部 Country：Japan
天然物を基盤とした新規UV-A吸収剤の合成とその機能

岩田愛紗、岩田隆幸、新藤充

第40回日本薬学会九州山口支部大会 2023.11

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Event date： 2023.11

Language：Japanese

Venue：第一薬科大学薬学部 Country：Japan
Ambidentアントラセンを利用したイプチセンの系統的合成

岩田隆幸、兵頭瑞樹、新藤充

第33回基礎有機化学討論会 2023.9

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Event date： 2023.9

Language：Japanese

Venue：岡山コンベンションセンター Country：Japan
分子内檜山カップリングを活用した1,8,13位異種置換トリプチセンの合成

岩田隆幸、花田将人、熊谷智、吉永達郎、塩田淑仁、吉澤一成、新藤充

第122回有機合成シンポジウム 2023.7

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Event date： 2023.6

Language：Japanese

Venue：東工大蔵前会館・くらまえホール Country：Japan
アミノトリプチセンの合成研究

賀來武志、岩田隆幸、新藤充

第60回化学関連支部合同九州大会 2023.6

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Event date： 2023.6

Language：Japanese

Venue：北九州国際会議場 Country：Japan
トリプチセンを土台としたシクロファンの合成

林優斗、前畑勇介、岩田隆幸、新藤充

第60回化学関連支部合同九州大会 2023.6

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Event date： 2023.6

Language：Japanese

Venue：北九州国際会議場 Country：Japan
脂質ミミックを目指したトリプチセン誘導体の合成

東恩納一樹、岩田隆幸、木下祥尚、松森信明、新藤充

第60回化学関連支部合同九州大会 2023.6

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Event date： 2023.6

Language：Japanese

Venue：北九州国際会議場 Country：Japan
ホスフィノトリプチセンの合成とその機能

波多江貴一、花田将人、岩田隆幸、新藤充

第60回化学関連支部合同九州大会 2023.6

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Event date： 2023.6

Language：Japanese

Venue：北九州国際会議場 Country：Japan
リチウムイオンを介した高度活性化ジビニルケトンのナザロフ反応

船津心吾、岩田隆幸、新藤充

日本薬学会第143年会 2023.3

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Event date： 2023.3

Language：Japanese

Venue：北海道大学 Country：Japan
mbidentアントラセンを用いた官能基化イプチセンの合成

川野隆生、兵頭瑞樹、岩田隆幸、新藤充

日本化学会第103春季年会(2023) 2023.3

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Event date： 2023.3

Language：Japanese

Venue：東京理科大学　野田キャンパス Country：Japan
環状イプチセンの合成研究

兵頭瑞樹、岩田隆幸、新藤充

日本化学会第103春季年会(2023） 2023.3

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Event date： 2023.3

Language：Japanese

Venue：東京理科大学　野田キャンパス Country：Japan
アンビデントアントラセンを利用した高次イプチセンの合成

兵頭瑞樹、岩田隆幸、新藤充

第121回有機合成シンポジウム 2022.11

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Event date： 2022.10 - 2022.11

Language：Japanese

Venue：早稲田大学国際会議場 Country：Japan
アンビデントアントラセン法を用いたイプチセンの合成

兵頭瑞樹、岩田隆幸、新藤充

第38回有機合成化学セミナー 2022.9

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Event date： 2022.9

Language：Japanese

Venue：アクティブリゾーツ福岡八幡 Country：Japan
トリプチセンのレトロFriedel-Crafts型開環と機能性芳香族分子の合成

川野隆生、深見拓人、岩田隆幸、新藤充

第38回有機合成化学セミナー 2022.9

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Event date： 2022.9

Language：Japanese

Venue：アクティブリゾーツ福岡八幡 Country：Japan
ジビニルケトンのルイス塩基性向上に基づく中性ナザロフ反応の開発

船津心吾、梶原康平、岩田隆幸、新藤充

第38回有機合成化学セミナー 2022.9

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Event date： 2022.9

Language：Japanese

Venue：アクティブリゾーツ福岡八幡 Country：Japan
トリプチセンのretro-Friedel-Crafts型開環とそのアセン合成への展開

川野隆生、深見拓人、岩田隆幸、新藤充

第32回万有福岡シンポジウム 2022.6

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Event date： 2022.6

Language：Japanese

Venue：九州大学椎木講堂 Country：Japan
ジビニルケトンの高度活性化による中性ナザロフ反応の開発

船津心吾、梶原康平、岩田隆幸、新藤充

第20回次世代を担う有機化学シンポジウム 2022.5

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Event date： 2022.5

Language：Japanese

Country：Japan
高活性化ジビニルケトンの中性ナザロフ反応における置換基効果

船津心吾、岩田隆幸、新藤充

日本薬学会第142年会 2022.3

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Event date： 2022.3

Language：Japanese Presentation type：Oral presentation (general)

Venue：オンライン Country：Japan
Synthesis of Iptycenes Using Ambident Anthracene

Mizuki Hyodo, Takayuki Iwata, Shindo Mitsuru

2022.3

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Event date： 2022.3

Language：English Presentation type：Oral presentation (general)

Country：Japan
トリプチセンのレトロFriedel-Crafts 型開環とそのアセン合成への応用

川野隆生、岩田隆幸、新藤充

日本化学会第102春季年会 (2022) 2022.3

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Event date： 2022.3

Language：Japanese Presentation type：Oral presentation (general)

Venue：オンライン Country：Japan
分子内檜山カップリングを基盤とした1,8,13 位異種置換トリプチセンの合成

花田将人、熊谷智、岩田隆幸、新藤充

日本化学会第102春季年会 (2022) 2022.3

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Event date： 2022.3

Language：Japanese Presentation type：Oral presentation (general)

Venue：オンライン Country：Japan
9-ヒドロキシトリプチセンのretro-Friedel-Crafts 型開環

川野隆生、深見拓人、岩田隆幸、新藤充

第3８回日本薬学会九州山口支部大会 2021.11

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Event date： 2021.11

Language：Japanese Presentation type：Oral presentation (general)

Venue：オンライン Country：Japan
檜山カップリングを用いた1,8,13 位異種置換トリプチセンの合成

花田将人、熊谷智、吉永達郎、岩田隆幸、新藤充

第3８回日本薬学会九州山口支部大会 2021.11

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Event date： 2021.11

Language：Japanese Presentation type：Oral presentation (general)

Venue：オンライン Country：Japan
高反応性アントラセンを利用した置換トリプチセンの効率合成

兵頭瑞樹, 深見拓人, 岩田隆幸, 塩田淑仁, 吉澤一成, 新藤充

第33回若手研究者のためのセミナー 2021.8

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Event date： 2021.8

Language：Japanese Presentation type：Oral presentation (general)

Venue：オンライン Country：Japan
近接効果による分子内活性化を利用した機能性トリプチセンの合成

花田将人, 熊谷智, 岩田隆幸, 新藤充

第33回若手研究者のためのセミナー 2021.8

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Event date： 2021.8

Language：Japanese Presentation type：Oral presentation (general)

Venue：オンライン Country：Japan
近接効果による分子内活性化を利用した機能性トリプチセンの合成

花田将人, 熊谷智, 岩田隆幸, 新藤充

第58回化学関連支部合同九州大会 2021.7

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Event date： 2021.7

Language：Japanese Presentation type：Oral presentation (general)

Venue：オンライン Country：Japan
高反応性アントラセンを利用した置換トリプチセンの効率合成

兵頭瑞樹, 深見拓人, 岩田隆幸, 塩田淑仁, 吉澤一成, 新藤充

第31回福岡万有シンポジウム 2021.6

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Event date： 2021.6

Language：Japanese Presentation type：Oral presentation (general)

Venue：オンライン Country：Japan
Synthesis of macrocyclic compounds using 1,8,13-substituted triptycenes　 as a foundation International conference

2021.3

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Event date： 2021.3

Language：English Presentation type：Oral presentation (general)

Venue：オンライン Country：Japan
トリプチサインを用いたイプチセンの合成

岩田　隆幸

第3回新学術領域研究「中分子戦略」第６回若手シンポジウム 2019.3

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Event date： 2020.2

Language：Japanese

Country：Japan
イノラートを用いたシン選択的なトリプチセンの合成

岩田隆幸、吉永達郎、梅津智、榮心勁、松本健司、新藤充

第3回新学術領域研究「中分子戦略」若手シンポジウム 2017.3

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Event date： 2020.2

Language：Japanese

Country：Japan
Synthesis of Syn-Substituted Triptycenes Using Triple-Cycloadditions of Arynes to Ynolates and their Transformations

Takayuki Iwata, Tatsuro Yoshinaga, Takumi Fujiwara, Takuto Fukami, Mitsuru Shindo

IRCCS-JST CREST Joint Symposium 2018.1

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Event date： 2020.2

Language：Japanese

Country：Japan
イノラートを用いたトリプチセンのワンポット合成とその変換

岩田隆幸、吉永達郎、藤原匠、深見拓人、新藤充

統合物質創製化学研究推進機構第 3 回国内シンポジウム 2017.10

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Event date： 2020.2

Language：English

Country：Japan
イノラート/アライン３連続環化付加反応を用いたイプチセンの合成

岩田隆幸、深見拓人、吉永達郎、新藤充

2018.10

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Event date： 2020.2

Language：Japanese

Country：Japan
Synthesis of Iptycenes Using Ynolate-Aryne Triple Cycloaddition International conference

Takayuki Iwata, Takuto Fukami, Tatsuro Yoshinaga, Takumi Fujiwara, Mitsuru Shindo

IRCCS The 2nd International Symposium 2019.1

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Event date： 2020.2

Language：Japanese

Country：Japan
ワンポットトリプチセン合成法を利用したイプチセンの合成研究

深見拓人、岩田隆幸、新藤充

第55回化学関連支部合同九州大会 2018.6

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Event date： 2018.6

Language：Japanese

Venue：北九州国際会議場 Country：Japan
ステモナアルカロイドの不斉全合成とその異性化解析

藤田聡, 富山泰至, 岩田隆幸, 松本健司, 新藤充

第47回複素環化学討論会 2017.10

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Event date： 2018.6

Language：Japanese

Country：Japan

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MISC

Cycloaddition Initiated by Ynolates: High-Energy Dianion Equivalents as a Molecular Glue Reviewed

Synlett 2022; 33(06): 531-545 2021.11

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Language：English Publishing type：Article, review, commentary, editorial, etc. (scientific journal)
Synthesis of 1,8,13-substituted triptycenes Reviewed

Takayuki Iwata, Mitsuru Shindo

Chem. Lett. 50, 39 (2021). 2021.6

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Language：English Publishing type：Article, review, commentary, editorial, etc. (scientific journal)
Synthesis, Stereochemical Stability, and Biological Activity of Stemonamine and Its Related Stemona Alkaloids

Takayuki Iwata and Mitsuru Shindo

Heterocycles 2019.3

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Language：English Publishing type：Article, review, commentary, editorial, etc. (scientific journal)

DOI： 10.3987/REV-19-902
電荷で決まる？歪で決まる？それとも？？－ベンザインの反応位置を予測できるか

岩田隆幸、新藤充

化学、化学同人 2017.7

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Language：Japanese Publishing type：Article, review, commentary, editorial, etc. (scientific journal)

Professional Memberships

The Society of Physical Organic Chemistry, Japan
Japanese Society for Chemical Biology
The chemical society of Japan

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The society of synthetic organic chemistry, Japan

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The Pharmaceutical Society of Japan

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Committee Memberships

天然物化学談話会世話人 Domestic

2023.8 - Present

Academic Activities

Screening of academic papers

Role(s)： Peer review

2024

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Type：Peer review

Number of peer-reviewed articles in foreign language journals：3
Screening of academic papers

Role(s)： Peer review

2023

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Type：Peer review

Number of peer-reviewed articles in foreign language journals：2
実行委員

第55回天然物化学談話会（オンライン） 2022.6

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Type：Competition, symposium, etc.
Screening of academic papers

Role(s)： Peer review

2022

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Type：Peer review

Number of peer-reviewed articles in foreign language journals：2
Screening of academic papers

Role(s)： Peer review

2021

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Type：Peer review

Number of peer-reviewed articles in foreign language journals：1

Number of peer-reviewed articles in Japanese journals：0

Proceedings of International Conference Number of peer-reviewed papers：0

Proceedings of domestic conference Number of peer-reviewed papers：0
Screening of academic papers

Role(s)： Peer review

2020

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Type：Peer review

Number of peer-reviewed articles in foreign language journals：1

Number of peer-reviewed articles in Japanese journals：0

Proceedings of International Conference Number of peer-reviewed papers：0

Proceedings of domestic conference Number of peer-reviewed papers：0
事務局

第29回万有福岡シンポジウム 2019.5

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Type：Competition, symposium, etc.
Screening of academic papers

Role(s)： Peer review

2019

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Type：Peer review

Number of peer-reviewed articles in foreign language journals：3

Number of peer-reviewed articles in Japanese journals：0

Proceedings of International Conference Number of peer-reviewed papers：0

Proceedings of domestic conference Number of peer-reviewed papers：0
実行委員

第60回天然有機化合物討論会 2018.9

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Type：Competition, symposium, etc.
Screening of academic papers

Role(s)： Peer review

2018

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Type：Peer review

Number of peer-reviewed articles in foreign language journals：3

Number of peer-reviewed articles in Japanese journals：0

Proceedings of International Conference Number of peer-reviewed papers：0

Proceedings of domestic conference Number of peer-reviewed papers：0
Screening of academic papers

Role(s)： Peer review

2017

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Type：Peer review

Number of peer-reviewed articles in foreign language journals：1

Number of peer-reviewed articles in Japanese journals：0

Proceedings of International Conference Number of peer-reviewed papers：0

Proceedings of domestic conference Number of peer-reviewed papers：0

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Research Projects

Development of Ambident Anthracene Method for Systematic Synthesis of Large Iptycenes

Grant number：23K04735 2023 - 2025

Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)

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Authorship：Principal investigator Grant type：Scientific research funding

CiNii Research
座標付き土台分子の開発と機能性分子空間の構築

2023 - 2025

旭硝子財団若手継続グラント

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Authorship：Principal investigator Grant type：Contract research
Development of Molecular Release Reaction based on Nazarov Reaction

Grant number：20K15283 2020 - 2022

Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Early-Career Scientists

Iwata Takayuki

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Authorship：Principal investigator Grant type：Scientific research funding

In this study, development of a "molecular release reaction," that can be used in biological environment, was investigated on the basis of Nazarov reaction. The conventional Nazarov reaction requires strong acids such as hydrochloric acid and this was a difficulty in applying the reaction to molecular release reactions. In order to improve the reactivity in the presence of weak acid, we designed a "highly activated divinyl ketone" based on the key concept of improving the Lewis basicity of divinyl ketone, lowering the activation energy for cyclization, and making the reaction irreversible by release of phenol. As a result, it was found that the Nazarov reaction proceeds not only in the presence of weak acid but also in neutral protic solvents such as methanol and water at room temperature. Thus, we successfully developed an unprecedented neutral Nazarov reaction.

CiNii Research
活性化アントラセンの生成を鍵とした環状イプチセンの合成

2019

ＱＲプログラムわかばチャレンジ

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Authorship：Principal investigator Grant type：On-campus funds, funds, etc.
ワンポットトリプチセン合成法を用いた高次イプチセン類の合成

2018 - 2019

旭硝子財団研究奨励

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Authorship：Principal investigator Grant type：Contract research
トリプチセンの開環反応を利用した“turn-on”型蛍光プローブの開発

2018

ＱＲプログラムわかばチャレンジ

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Authorship：Principal investigator Grant type：On-campus funds, funds, etc.
イノラート・アライン３連続環化付加反応を用いたイプチセン類のモジュラー合成

Grant number：17K14449 2017 - 2019

科学研究費助成事業若手研究(B)

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Authorship：Principal investigator Grant type：Scientific research funding

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Class subject

有機機器分析

2024.4 - 2024.9 First semester
分子の科学

2023.4 - 2023.9 First semester
分子の科学

2022.4 - 2022.9 First semester
有機機器分析

2022.4 - 2022.9 First semester
エネルギー物質工学実験Ⅰ

2022.4 - 2022.9 First semester
有機機器分析

2021.4 - 2021.9 First semester
分子の科学

2021.4 - 2021.9 First semester
エネルギー物質工学実験Ⅰ

2021.4 - 2021.9 First semester
有機機器分析

2020.4 - 2020.9 First semester
エネルギー物質工学実験Ⅰ

2020.4 - 2020.9 First semester
有機機器分析

2019.4 - 2019.9 First semester
分子の科学

2019.4 - 2019.9 First semester
エネルギー物質工学実験Ⅰ

2019.4 - 2019.9 First semester
有機機器分析

2018.4 - 2018.9 First semester
分子の科学

2018.4 - 2018.9 First semester
エネルギー物質工学実験Ⅰ

2018.4 - 2018.9 First semester
有機機器分析

2017.4 - 2017.9 First semester
分子の科学

2017.4 - 2017.9 First semester
エネルギー物質工学実験Ⅰ

2017.4 - 2017.9 First semester
有機機器分析

2016.4 - 2016.9 First semester
分子の科学

2016.4 - 2016.9 First semester
エネルギー物質工学実験Ⅰ

2016.4 - 2016.9 First semester

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FD Participation

2023.2 Role：Participation Title：令和４年度先導研FD研修会

Organizer：[Undergraduate school/graduate school/graduate faculty]
2022.1 Role：Participation Title：令和３年度先導研FD研修会

Organizer：[Undergraduate school/graduate school/graduate faculty]
2021.1 Role：Participation Title：令和２年度第１回先導研FD研修会

Organizer：[Undergraduate school/graduate school/graduate faculty]
2020.1 Role：Participation Title：平成31年度第２回先導研FD研修会

Organizer：[Undergraduate school/graduate school/graduate faculty]
2019.5 Role：Participation Title：平成31年度第１回先導研FD研修会

Organizer：[Undergraduate school/graduate school/graduate faculty]
2018.7 Role：Participation Title：平成30年度第１回先導研FD研修会

Organizer：[Undergraduate school/graduate school/graduate faculty]
2018.1 Role：Participation Title：平成29年度第２回先導研FD研修会

Organizer：[Undergraduate school/graduate school/graduate faculty]
2018.1 Role：Participation Title：平成30年度第２回先導研FD研修会

Organizer：[Undergraduate school/graduate school/graduate faculty]
2017.5 Role：Participation Title：平成29年度第１回先導研FD研修会

Organizer：[Undergraduate school/graduate school/graduate faculty]
2016.12 Role：Participation Title：平成28年度第２回先導研FD研修会

Organizer：[Undergraduate school/graduate school/graduate faculty]
2016.5 Role：Speech Title：平成28年度第１回先導研FD研修会

Organizer：[Undergraduate school/graduate school/graduate faculty]

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Travel Abroad

2015.5 - 2016.3

Staying countory name 1：United States Staying institution name 1：Boston University