Synthetic study of polycyclic natural products having adjacent quaternary asymmetric carbon atoms toward the understanding of their biological effects

2014 Fiscal Year Final Research Report

• Project/Area Number: 24510290
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Living organism molecular science
• Research Institution: Hokkaido University
• Principal Investigator: YOSHIMURA Fumihiko 北海道大学, 理学(系)研究科(研究院), 助教 (70374189)
• Project Period (FY): 2012-04-01 – 2015-03-31
• Keywords: 全合成 / ブラシリカルジン / アンドラスチン / ニトリル / ニトロン / 四級不斉炭素 / N-シリルケテンイミン

Outline of Final Research Achievements

This research aimed at total syntheses of Brasilicardin A and Andrastin C that belong to biologically active natural products with adjacent and/or contiguous quaternary asymmetric carbon atoms on their polycyclic frameworks. To achieve this goal, we developed an efficient synthetic method for stereoselective construction of a quaternary asymmetric carbon atom through an intramolecular conjugate addition reaction of α-cyano carbanion. By using this method as key reactions, we succeeded in the synthesis of methyl ester of Brasilicardin A aglycon. Additionally, novel nucleophilic addition reactions of nitriles to nitrones under mild silylation conditions were developed.

Free Research Field

天然物合成化学