Development of new reactions using the properties of butenolide and the synthetic study on gibberellins

2023 Fiscal Year Final Research Report

• Project/Area Number: 21K06481
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Review Section: Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
• Research Institution: Kitasato University
• Principal Investigator: Ohtawa Masaki 北里大学, 薬学部, 准教授 (70453503)
• Project Period (FY): 2021-04-01 – 2024-03-31
• Keywords: 有機合成化学 / ラジカル反応 / 天然物合成

Outline of Final Research Achievements

Applying butenolide's characteristic radical/polar reaction, a five-membered α,β-unsaturated lactone, has led to a multifaceted study. We found oxidative radical dimerization reactions of butenolide. Subsequent substrate scope for various butenolides revealed that this reaction has a broad substrate generality. On the other hand, the Michael/Michael/Dieckmann tandem cyclization of γ-arylbutenolides led to the construction of a 6-5-6-5 fused ring skeleton in one step, yielding a common intermediate of the gibberellins.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

本研究成果により、ブテノリドのビルディングブロックとしてのポテンシャルを飛躍的に広げることが可能となった。すなわち今回見出したブテノリドラジカルの酸化的ダイマー化反応を応用することで、ブテノリドダイマー型天然物の効率的な合成が可能となるだけでなく、ブテノリド特有の極性反応を駆使することで、gibberellin類のような生物活性物質の真に効率的な天然物の合成法の提案が可能になった。