Synthetic study of indolalkaloids using a [3+3] cycloaddition reaction

2015 Fiscal Year Final Research Report

• Project/Area Number: 25460019
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Nagoya City University
• Principal Investigator: Kato Nobuki 名古屋市立大学, 薬学研究科(研究院), 講師 (50400221)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: インドールアルカロイド / 分子内酸化的カップリング / かご型構造

Outline of Final Research Achievements

Scholarisine A, isolated from the leaves of Alstonia scholaris, is a monoterpene indole alkaloid with an unprecedented cage-like structure. In this paper, preparation of the distinctive cage-like core skelton of the Scholarisine A is described. The key feature of this synthetic strategy is an intramolecular oxidative coupling reaction at the late stage to construct a 10-oxa-tricyclo[5.3.1.03,8]undecan-9-one structure fused with indolenine. Intramolecular oxidative coupling using N-iodosuccinimide gave the carbon framework of Scholarisine A in moderate yield, which is the first example of intrarmolecular oxidative coupling reaction between non-activated enolate and indole. This study lays the foundation for continued investigations toward the total synthesis of Scholarisine A.

Free Research Field

天然物合成