Stereoselective synthesis of the bicyclo[5.3.0]decane portion of the diterpene antibiotic guanacastepene using a pyrylium-ylide [5+2] cycloaddition reaction

被引:52
作者
Magnus, P [1 ]
Waring, MJ [1 ]
Ollivier, C [1 ]
Lynch, V [1 ]
机构
[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
关键词
guanacastepene; antibiotic; pyrylium-ylide; conjugate addition;
D O I
10.1016/S0040-4039(01)00851-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of 14 with Ac2O/Et3N resulted in [5+2] cyclization to give 2, which was further elaborated into 20, thus establishing the required stereochemistry in the top-half of guanacastepene 1. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4947 / 4950
页数:4
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