Catalytic asymmetric synthesis of either enantiomer of the Calabar alkaloids physostigmine and physovenine

被引：234

作者：

Matsuura, T ^{[1
]}

Overman, LE ^{[1
]}

Poon, DJ ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1998年 / 120卷 / 26期

关键词：

D O I：

10.1021/ja980788+

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A potentially versatile asymmetric route to hexahydropyrrolo[2,3-b]indoles having carbon substituents at C-3a (Scheme 1) is demonstrated through enantioselective total syntheses of the Calabar alkaloids.(-)-physostigmine (2), (-)-physovenine (10), and their enantiomers. The synthesis of enantiopure (-)physostigmine proceeds from commercially available 2-butyn-1-ol (11) and N-methyl-p-anisidine (15) in 15-20% overall yield by way of eight isolated and purified intermediates. The central step is catalytic asymmetric Heck cyclization of (Z)-2-methyl-2-butenanilide 17 to form oxindole aldehyde (S)-19 in 84% yield and 95% ee.

引用

页码：6500 / 6503

页数：4

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