KEIO RESEARCHERS INFORMATION SYSTEM

Message from the Faculty Member 【 Display / hide 】

Message from the Faculty Member 【 Display / hide 】

• 創薬化学を中心に、より有用で機能的な有機分子を求め、合成する化合物の複雑化が急速に進行しています。我々は、化学的な独創性と、社会的に需要の高まった複雑な化合物に適用できる実用性を同時に満たす合成手法を開発し、それを用いて重要な生物活性を有する天然物の全合成を精力的に行っていきます。

Career 【 Display / hide 】

Career 【 Display / hide 】

• 2003.07

  -

  2003.08

  スイス連邦工科大学　21世紀COE海外研究拠点・研究員

• 2005.04

  -

  2006.03

  日本学術振興会特別研究員（DC2）

• 2006.04

  -

  2007.03

  日本学術振興会特別研究員（PD）

• 2007.04

  -

  2008.03

  カリフォルニア大学アーバイン校・博士研究員

• 2008.04

  -

  2010.03

  慶應義塾大学　助教（有期）（理工学部応用化学科）

display all >>

Academic Background 【 Display / hide 】

Academic Background 【 Display / hide 】

• 2001.03

  Tohoku University, Faculty of Science

  University, Graduated

• 2006.03

  Tohoku University, Graduate School, Division of Natural Science

  Graduate School, Completed, Doctoral course

Academic Degrees 【 Display / hide 】

Academic Degrees 【 Display / hide 】

• 博士（理学）, Tohoku University, Coursework, 2006.03

  Asymmetric Total Synthesis of (-)-Merrilactone A

Research Areas 【 Display / hide 】

Research Areas 【 Display / hide 】

• Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry (Organic Chemistry)

• Life Science / Bioorganic chemistry (Organic Chemistry)

Research Keywords 【 Display / hide 】

Research Keywords 【 Display / hide 】

• 天然物化学

• 有機合成化学

Research Themes 【 Display / hide 】

Research Themes 【 Display / hide 】

• スキップジエン構築法の開発と天然物合成への応用, 

  2010.04

  -

  Present

• アミド基変換反応の開発, 

  2008.04

  -

  Present

Books 【 Display / hide 】

Books 【 Display / hide 】

• Nucleophilic addition to amides toward efficient total synthesis of complex alkaloids

  Sato T., New Tide of Natural Product Chemistry, 2023.06

  　View Summary

  Nucleophilic addition to amides has been recognized as a promising transformation for the total synthesis of polycyclic alkaloids. The reaction produces substituted amines from easily available amides while avoiding the unwanted high reactivities of amines and use of extra-protecting group manipulations. In this chapter, we introduce the development of two types of amide-selective nucleophilic addition reactions and their applications to total synthesis. The first topic is the total synthesis of gephyrotoxin based on the reductive allylation of an N-methoxylactam. The reaction takes place in the presence of a more electrophilic methyl ester by taking advantage of the N-methoxy group and the Schwartz reagent [Cp<Subscript>2</Subscript>ZrHCl]. The second topic is the unified total synthesis of stemoamide-type alkaloids by chemoselective assembly of five-membered rings. The most challenging step is an iridium-catalyzed reductive nucleophilic addition to a γ-lactam. A γ-lactone was installed to a γ-lactam carbonyl without affecting the γ-lactone found in tetracyclic protostemonamide, resulting in the total synthesis of pentacyclic protostemonines.

  • Access to Document (DOI)

• ドラマチック有機合成化学 感動の瞬間100

  佐藤隆章, 化学同人, 2023,  Page： 142-143

• New Tide of Natural Product Chemistry

  Takaaki Sato, Springer, 2023,  Page： 275‒293

• Comprehensive Chirality

  SATOU Takaaki, Elsevier Science, 2012.10

  Scope: 207‒239

• 天然物合成で活躍した反応 実験のコツとポイント

  井上将行, 佐藤隆章, 化学同人, 2011.11

  Scope: 62-63

display all >>

Papers 【 Display / hide 】

Papers 【 Display / hide 】

• Computational Study Focusing on a Comprehensive Conformational Analysis of Transition States for Aza-Spiro Ring Formations with N-Alkoxyamides

  Fukaya K., Sato T., Chida N., Urabe D.

  Journal of Organic Chemistry （Journal of Organic Chemistry)  88 （ 19 ） 13655 - 13665 2023.10

  ISSN  00223263

  　View Summary

  An accurate understanding of conformations in transition states is a critical piece in the theoretical analysis of complex molecular reactions. In this study, we investigated conformationally diverse transition states during intramolecular aza-spiro ring formation with an allylsilane moiety and N-alkoxy iminium ion, a key reaction in the synthesis of fasicularin by Sato and Chida et al., and identified the origins of stereoselectivity of the cyclization. A large number of conformational isomers with forming C-C bonds were comprehensively analyzed using Cremer-Pople puckering parameters. It was found that the conformations of the transition states had different puckering preferences depending on the reactant’s double-bond geometry and the product’s stereochemical configuration. Furthermore, an asymmetric aza-spiro cyclization with a tolyl group as a chiral auxiliary was investigated, showing that conformational anchoring by both a CH-O hydrogen bond and the CH−π interaction was critical for the asymmetric induction.

  • Access to Document (DOI)

• Synthesis and Evaluation of Saponins with All-Nitrogenated Sugars

  Kage A., Okuyama Y., Kato E., Matagawa T., Kawano S., Simizu S., Chida N., Okamura T., Sato T.

  Synlett （Synlett)   2023

  ISSN  09365214

  　View Summary

  Saponins exhibit multiple biological and pharmacological activities, and the sugar moiety of saponins is known to play a crucial role in bioactivity. In this report, we focus on the synthesis and evaluation of saponins with all-nitrogenated sugar (ANS), in which all oxygen atoms are replaced with nitrogen atoms. OSW-1 derivative-, cholesterol-,and diosgenin-ANS glycosides are synthesized by glycosylation with ANS in the presence of TMSOTf. As a result, the OSW-1 mimic, with ANS, exhibits good cytotoxic activity (IC50 = 7.31 ?M) and induces apoptosis.

  • Access to Document (DOI)

• Synthesis of Chiral α, α-Disubstituted Cyclic Nitrones from Secondary Lactams

  Iwamoto S., Tokuyama A., Hiraoka S., Takei K., Matsuzaka K., Matsumoto T., Chida N., Sato T.

  Bulletin of the Chemical Society of Japan （Bulletin of the Chemical Society of Japan)  96 （ 6 ） 529 - 537 2023

  ISSN  00092673

  　View Summary

  Synthesis of chiral α, α-disubstituted cyclic nitrones from secondary lactams is reported. The method consists of two stages involving N-oxidation of the lactams and nucleophilic addition to the lactam carbonyls. The N-oxidation of secondary lactams with mCPBA via imidates provides cyclic nitrones with a chiral stereocenter adjacent to the nitrogen atom. A variety of α, α-disubstituted cyclic nitrones were quickly obtained simply by changing organolithium reagents in the nucleophilic addition to N-OSEM lactams.

  • Access to Document (DOI)

• Iridium-catalyzed Reductive Olefination of N-Methoxyamides

  Iiyama S., Mizutani K., Sato T.

  Chemistry Letters （Chemistry Letters)  52 （ 8 ） 682 - 684 2023

  ISSN  03667022

  　View Summary

  An iridium-catalyzed reductive olefination of N-methoxyamides in a one-pot process is reported. The method begins with hydrosilylation of an amide carbonyl. The O-Si bond in the resulting N,O-silylacetal is then cleaved under mild conditions with TBACl to give an aldehyde, which undergoes various types of Wittig reactions in a highly stereoselective manner. The method is successfully applied to the construction of dienoates, which are widely observed in biologically active polyketides.

  • Access to Document (DOI)

• Iridium-Catalyzed Reductive (3+2) Annulation of Lactams Enabling the Rapid Total Synthesis of (±)-Eburnamonine

  Sugiyama Y., Yamada K., Kaneko D., Kusagawa Y., Okamura T., Sato T.

  Angewandte Chemie - International Edition （Angewandte Chemie - International Edition)   2023

  ISSN  14337851

  　View Summary

  A reductive (3+2) annulation of lactams through iridium-catalyzed hydrosilylation and photoredox coupling with α-bromoacetic acid was developed. The iridium-catalyzed hydrosilylation of the lactam carbonyl group and subsequent elimination provide a transient cyclic enamine, which undergoes iridium-catalyzed photoredox coupling with α-bromoacetic acid in a one-pot process. The developed conditions show high functional-group tolerance and provide cyclic N,O-acetals containing a quaternary carbon center. The resulting N,O-acetals undergo a variety of acid-mediated nucleophilic addition reactions via iminium ions to give substituted cyclic amines. The developed sequence including reductive (3+2) annulation and acid-mediated nucleophilic addition was successfully applied to the four-step total synthesis of (±)-eburnamonine.

  • Access to Document (DOI)

display all >>

Papers, etc., Registered in KOARA 【 Display / hide 】

Papers, etc., Registered in KOARA 【 Display / hide 】

• Synthesis of 1,3-dipoles from amides

  Satō, Takaaki

  科学研究費補助金研究成果報告書 2020

• Transformation of amides by using an N-alkoxy group as a reactivity control element

  Sato, Takaaki

  科学研究費補助金研究成果報告書 2017

• Development of direct nucleophilic addition to inert amides

  Sato, Takaaki

  科学研究費補助金研究成果報告書 2014

• Development and application of practical methodology to access biologically active alkaloids using alkoxyamide

  Sato, Takaaki

  科学研究費補助金研究成果報告書 2011

Presentations 【 Display / hide 】

Presentations 【 Display / hide 】

• Amides Enabling Efficient Synthesis of Alkaloids

  Takaaki Sato

  International Symposium for the 80th Anniversary Symposium of the Tohoku Branch Chemical Society, 

  2023.09

• Unified Total Synthesis of Stemoamide-Type Alkaloids Based on the Amide-Selective Nucleophilic Addition

  Takaaki Sato

  The 11th Singapore International Chemistry Conference, 

  2022.12

• 複雑分子の合成効率化を目指して

  佐藤隆章

  ヘテロ原子部会2022年度第2回懇話会, 

  2022.12

• 天然物全合成の効率化について考えてみた

  佐藤隆章

  第55回天然物談話会, 

  2022.06

• 複雑化合物の超短工程合成を実現するには

  佐藤隆章

  静岡県立大学大学院特別講義, 

  2021.11

display all >>

Research Projects of Competitive Funds, etc. 【 Display / hide 】

Research Projects of Competitive Funds, etc. 【 Display / hide 】

• 超短工程化アミド戦略による多環性アルカロイドの合成効率化

  2022.04

  -

  2027.03

  文部科学省・日本学術振興会, 基盤B, Research grant, Principal investigator

• プロリン・N-メチルアミノ酸選択的なペプチド直接修飾法の開発

  2022.04

  -

  2024.03

  旭硝子財団, 研究奨励, Research grant, Principal investigator

• ポリケチド医薬品の完全化学合成を目指して

  2021.12

  -

  2023.09

  アステラス病態代謝研究会, 研究助成金, Research grant, Principal investigator

• アミド基を基盤としたポリケチド合成法の開発

  2021.11

  -

  2022.11

  12. 住友財団, 基礎科学研究助成, Research grant, Principal investigator

• 反復ブロック合成法による多環性機能分子の創製

  2020

  天野工業技術研究所, 天野工業技術研究所研究助成金, Research grant, Principal investigator

display all >>

Awards 【 Display / hide 】

Awards 【 Display / hide 】

• Thieme Chemistry Journals Award

  2019

  Type of Award： International academic award (Japan or overseas)

• BCSJ award

  2017.08, Reductive Approach to Nitrones from N-Siloxyamides and N-Hydroxyamides

• International Symposium on Pure & Applied Chemistry 2017, Lecture Award

  2017.06, Unified Total Synthesis of Stemoamide-Type Alkaloids

• Incentive Award in Synthetic Organic Chemistry, Japan

  佐藤隆章, 2017.02, 有機合成化学協会, 反応性制御素子を用いたアミド変換反応の開発と応用

  Type of Award： Award from Japanese society, conference, symposium, etc.

• BCSJ award

  2015.04, 日本化学会, Total Syntheses of (±)-Gephyrotoxin and (±)-Perhydrogephyrotoxin

display all >>

Courses Taught 【 Display / hide 】

Courses Taught 【 Display / hide 】

• SEMINAR IN APPLIED CHEMISTRY

  2024

• ORGANIC CHEMISTRY

  2024

• MECHANISM IN ORGANIC CHEMISTRY

  2024

• LABORATORY IN SCIENCE

  2024

• LABORATORIES IN APPLIED CHEMISTRY B

  2024

display all >>

Memberships in Academic Societies 【 Display / hide 】

Memberships in Academic Societies 【 Display / hide 】

• 日本プロセス化学会, 

  2015.03

  -

  Present

• 日本薬学会, 

  2015.03

  -

  2020.03

• American Chemical Society, 

  2013

  -

  Present

• 慶應有機合成化学若手シンポジウム委員会, 

  2012.12

  -

  2022.03

• 全国高校化学グランプリ委員会, 

  2011

  -

  2012

display all >>

Committee Experiences 【 Display / hide 】

Committee Experiences 【 Display / hide 】

• 2015.12

  -

  2016.05

  実行委員長, 慶應有機化学若手シンポジウム

• 2015.03

  -

  Present

  会員, 日本プロセス化学会

• 2015.03

  -

  2023.03

  プロセス化学会将来計画委員, 日本プロセス化学会

• 2015.03

  -

  2019.12

  会員, 日本薬学会

• 2013

  -

  Present

  member, American Chemical Society

display all >>