The remarkable effect of cosolvent on a samarium(II)-mediated 4-exo-trig cyclization:: Further synthetic studies on pestalotiopsin A

被引：64

作者：

Edmonds, DJ ^{[1
]}

Muir, KW ^{[1
]}

Procter, DJ ^{[1
]}

机构：

[1] Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 08期

关键词：

D O I：

10.1021/jo026827o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A samarium(II)-mediated 4-exo-trig cyclization in which a remote stereocenter serves to control the facial selectivity of the cyclization is described. The apparent coordination of a tert-butyldimethylsilyl ether to the samarium center appears to give rise to the selectivity. The remarkable effect of the cosolvent, 2,2,2-trifluoroethanol, on the cyclization of this substrate, is also discussed. A stereoselective synthesis of the general class of gamma,delta-unsaturated aldehyde cyclization substrate is reported, and the utility of the cyclization is demonstrated in an approach to the fully functionalized core of pestalotiopsin A.

引用

页码：3190 / 3198

页数：9

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