Innovative approach to illisimonin A by one-step multi-ring construction strategy

2022 Fiscal Year Final Research Report

• Project/Area Number: 20K05485
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Review Section: Basic Section 33020:Synthetic organic chemistry-related
• Research Institution: Hokkaido University
• Principal Investigator: Suzuki Takahiro 北海道大学, 理学研究院, 准教授 (80367052)
• Project Period (FY): 2020-04-01 – 2023-03-31
• Keywords: 天然物合成 / セスキテルペン / Diels-Alder反応 / ビシクロ[2.2.1]ヘプタン

Outline of Final Research Achievements

A number of natural organic compounds with sterically complex fused ring structures (higher-order structures) exhibit useful biological activities. Illisimonin A, which was recently reported to be isolated from nature, possesses a higher-order structure and, together with its biological activity, has attracted the interest of numerous scientists. The aim of this study was the efficient total synthesis of Illisimonin A based on the "one-step multiple ring construction strategy" proposed by the applicant.
Based on the presumed biosynthetic pathway of Illisimonin A, the intramolecular Diels-Alder reaction of orthobenzoquinone and the subsequent benzylic acid rearrangement were set as the key reactions, and the practical synthesis using model compounds was successfully performed to obtain the Illisimonin A skeleton.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

本研究により、天然物であるイリシモニンAの骨格の合成に成功したことから、天然物の生合成経路を理解する上での学術的意義がある。また、天然物から新規な医薬品を開発するためには、天然物の全合成が必要であり、本研究によりイリシモニンAの効率的な合成法が確立されたことで、医薬品開発に対する社会的意義がある。さらに、本研究で提案された一段階多重環構築戦略は、他の天然物の合成にも応用できる可能性があり、有機合成化学の有用な技術基盤となることが期待される。