Utilization of a Michael addition:: Dipolar cycloaddition cascade for the synthesis of (±)-cylindricine c

被引：43

作者：

Flick, Andrew C. ^{[1
]}

Caballero, Maria Jose Arevalo ^{[1
]}

Padwa, Albert ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 09期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1021/ol8006056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new approach to the marine alkaloid (+/-)-cylindricine C has been devised. The key element of the synthesis consists of a Michael addition/dipolar cycloaddition cascade between 2,3-bis(phenyisulfonyl)-1,3-butadiene and 9-triisopropylsilanyloxy-non-l-en-5-one oxime. The resulting cycloadduct was converted into (+/-)-cylindricine C by a sequence of reactions including a reductive cyclization, intramolecular enolate alkylation, and conjugate addition to introduce the n-hexyl side chain.

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页码：1871 / 1874

页数：4

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