Total synthesis of (-+)-stenine using the IMDAF cycloaddition of a 2-methylthio-5-amido-substituted furan

被引：96

作者：

Ginn, JD ^{[1
]}

Padwa, A ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 09期

关键词：

D O I：

10.1021/ol025746b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular [4 + 2]-cycloaddition of a 2-methylthio-5-amidofuran was used to create the azepinoindole skeleton present in the Stemona alkaloid stenine. The rearranged cycloadduct was converted to stenine (1) in 11 additional steps via a sequence that features a Crabtree catalyst directed hydrogenation (9-->10), iodolactonization (2-->11), and a Keck allylation (11-->12).

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页码：1515 / 1517

页数：3

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