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

Ze-Xin Zhang; Si-Cong Chen; Lei Jiao

doi:10.1055/s-0036-1589075

Synlett, Inhaltsverzeichnis

Synlett 2017; 28(17): 2199-2204
DOI: 10.1055/s-0036-1589075

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

Ze-Xin Zhang

Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China eMail: leijiao@mail.tsinghua.edu.cn

,

Si-Cong Chen

Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China eMail: leijiao@mail.tsinghua.edu.cn

,

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

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Abstract

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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.

Key words

alkaloids - indoles - minfiensine - asymmetric cascade cyclization - asymmetric allylic alkylation - palladium catalysis

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Referenzen

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