Highly selective entry to the azadirachtin skeleton via a Claisen rearrangement/radical cyclization sequence

被引：62

作者：

Durand-Reville, T ^{[1
]}

Gobbi, LB ^{[1
]}

Gray, BL ^{[1
]}

Ley, SV ^{[1
]}

Scott, JS ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 22期

关键词：

D O I：

10.1021/ol0201557

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

graphic A highly diastereoselective, microwave-induced Claisen rearrangement of an appropriately substituted propargylic enol ether allows the formation of the sterically congested C-8-C-14 bond of azadirachtin. When combined with a radical-mediated cyclization of the corresponding allene, this sequence offers rapid entry to the framework of azadirachtin.

引用

页码：3847 / 3850

页数：4

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