Synthesis of optically active tetralones based on organocatalytic kinetic resolution

2018 Fiscal Year Final Research Report

• Project/Area Number: 16K17897
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Tokyo University of Agriculture and Technology
• Principal Investigator: Odagi Minami 東京農工大学, 工学(系)研究科(研究院), 助教 (30772157)
• Project Period (FY): 2016-04-01 – 2019-03-31
• Keywords: 有機触媒 / 光学分割 / テトラロン / 酸化反応 / リシリリドB / グアニジン / ウレア

Outline of Final Research Achievements

We have investigated that development of oxidative kinetic resolution of tetralones by using organocatalyst for providing an optically active tetralones. In this project, oxidative kinetic resolution of tetralone-derived beta-ketoester based on enantioselective alpha-hydroxylation by using guanidine-bisurea bifunctional organocatalyst was developed, and the reaction was applied to synthetic study of rishirilide B. As a result, we have achieved to synthesize both enantiomers of natural product, and the absolute configuration of natural (+)-rishirilide B was revised by chiral HPCL analysis.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

テトラロン構造は有用な生理活性を示す天然物や医農薬品の合成中間体に広く見出される構造である。本研究では、光学活性な当該構造を効率的に合成する手法として、有機触媒を用いた速度論的光学分割反応を開発した。これにより新規創薬リード化合物の効率的な合成が可能となる。