Development of a method for the preparation of optically active tetrasubstituted allenes via dynamic kinetic resolution: its application to syntheses of natural products

2017 Fiscal Year Final Research Report

• Project/Area Number: 15K07864
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: University of Shizuoka
• Principal Investigator: Egi Masahiro 静岡県立大学, 食品栄養科学部, 教授 (80363901)
• Co-Investigator(Kenkyū-buntansha): 菅 敏幸 静岡県立大学, 薬学部, 教授 (10221904)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Keywords: アレン / 天然物合成 / 有機合成化学 / プロパルギルアルコール / シグマトロピー転位 / 分子内環化 / インデン

Outline of Final Research Achievements

Our efficient synthesis of tetrasubstituted allenes was applied to total synthetic studies on natural products. In the synthesis of raputindole A, the allene obtained underwent the intramolecular cyclization to give the tricyclic skeleton. Chelation-controlled reduction was carried out, followed by the introduction of side chains to access raputindole A. Moreover, tetrasubstituted allene was synthesized as a key intermediate toward the total synthesis of taiwaniaquinol D.
In order to develop a synthesis of optically active tetrasubstituted allenes using dynamic kinetic resolution, a racemization catalyst of propargyl alcohols and a chiral silver catalyst that catalyzes sigmatropic rearrangement were investigated.

Free Research Field

医歯薬学