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2020 Fiscal Year Final Research Report

Development of novel reactions induced by rare earth elements and titanium for the construction of carbon skeletons and synthetic studies of bioactive compounds

Research Project

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Project/Area Number 18K05130
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionMeiji Pharmaceutical University

Principal Investigator

Takatori Kazuhiko  明治薬科大学, 薬学部, 教授 (30231393)

Project Period (FY) 2018-04-01 – 2021-03-31
Keywordsラジカル反応 / 骨格形成 / サマリウム / チタン / テルペン / 転位反応
Outline of Final Research Achievements

In this study, the development of novel skeletal formation reactions induced by rare earth elements and titanium and the total synthesis of biologically active compounds were investigated. The following results were obtained. 1) Ring-expanding reaction of α-(mesyloxymethyl)cyclobutanones was developed. 2) A diastereomer of zoapatlin was synthesized by SmI2-mediated sequential cyclization and ring-expanding 1,2-rearrangement reaction. 3) The formal synthesis of hypnophilin was achieved by repeated ring-expanding 1,2-rearrangement and oxidative allylic rearrangement. 4) Intramolecular cyanohydrin-epoxide coupling reaction with low-valent Ti was developed, and the total synthesis of marsupellin A was achieved.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

天然物には、医薬資源として有用であるにも関わらず、供給困難で複雑な骨格構造を持った化合物が多い。そのような化合物の効率良い合成法の開発は、新たな医薬シードの提供に繋がる。複雑な骨格構造を効率よく構築するためには、新規な骨格形成反応の開発が欠かせない。この研究では、金属を用いた還元反応を起点とした新規骨格形成反応の開発と生物活性化合物の全合成を検討した。その結果、チタンと希土類金属であるサマリウムを用いた反応を開発することができ、アルツハイマー病の対処療法に有効とされるコリンエステラーゼ阻害活性を示すマルスペリン類など5つの天然物の初の全合成に成功した。

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Published: 2022-01-27  

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