Total synthesis of natural products with unique and complex structures based on transformation of multi-substituted cyclopropanes

2020 Fiscal Year Final Research Report

• Project/Area Number: 17H05051
• Research Category: Grant-in-Aid for Young Scientists (A)
• Allocation Type: Single-year Grants
• Research Field: Chemical pharmacy
• Research Institution: Kyoto University
• Principal Investigator: Tsukano Chihiro 京都大学, 農学研究科, 准教授 (70524255)
• Project Period (FY): 2017-04-01 – 2021-03-31
• Keywords: 合成化学 / 有機化学 / 生理活性 / 全合成 / 天然物化学

Outline of Final Research Achievements

Synthetic studies of complex, unique, and challenging structures are important because they create new methodologies. In this study, we have developed a synthetic strategy for a multi-substituted three-membered ring including all-cis substituted cyclopropane, which has not been focused on so far. Based on these originally developed strategies, we have achieved the total synthesis of natural products with complex structures. In particular, the first total syntheses of non-canonical strigolactone, avenaol and lycopodium alkaloid lyconesidine B showing antitumor activity were accomplished. In addition, we have investigated concise synthesis of polycyclic alkaloids, and successfully developed several new synthetic strategies.

Free Research Field

有機合成化学、天然物全合成

Academic Significance and Societal Importance of the Research Achievements

近年、再興感染症が社会問題となっており、将来治療が困難な多剤耐核菌が増加することが予測されており、新たな作用機序をもつ薬物開発が喫緊の課題となっている。本研究により、複雑な骨格を有する天然物で、新規作用機序を有するものの試料供給を可能とするだけでなく、自然界から得ることのできない類縁体の供給を合成化学的に可能とした。これにより、活性発現に重要な構造を明らかにするとともに、これら天然物の新規薬剤としての可能性を検討するための足がかりを得た。