Synlett 2017; 28(17): 2199-2204
DOI: 10.1055/s-0036-1589075
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© Georg Thieme Verlag Stuttgart · New York

Asymmetric Total Synthesis of (+)-Minfiensine by an Asymmetric Cascade Cyclization Strategy

Ze-Xin Zhang, Si-Cong Chen, Lei Jiao*
  • Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China   Email: leijiao@mail.tsinghua.edu.cn
Financial support from the National Natural Science Foundation of China (Grant No. 21502102) and the Thousand Talents Plan for Young Professionals is acknowledged.
Further Information

Publication History

Received: 27 May 2017

Accepted after revision: 19 June 2017

Publication Date:
25 August 2017 (eFirst)

Abstract

The Strychnos alkaloid minfiensine and a series of akuammiline alkaloids, such as vincorine, aspidophylline A, and picrinine, possess a common core skeleton, a 4a,9a-heterocycle-fused tetrahydrocarbazole. Efficient construction of this core structure in a highly enantioselective manner would facilitate the total synthesis of these alkaloids. In this article, we briefly summarize the established strategies for obtaining this core structure, together with the corresponding total-synthesis routes, and we describe our own effort on the development of a new strategy, the asymmetric cascade dearomative cyclization, for the efficient total synthesis of (+)-minfiensine.