BROMINE ADDITION TO ALPHA-(1-HYDROXYALKYL)-ALPHA,BETA-UNSATURATED ESTERS AND ALPHA-(1-ALKOXYALKYL)-ALPHA,BETA-UNSATURATED ESTERS - AN APPROACH TO HYDROXYFIMBROLIDE AND BROMOBECKERELIDE

被引：5

作者：

CALDERON, A ^{[1
]}

FONT, J ^{[1
]}

DEMARCH, P ^{[1
]}

机构：

[1] UNIV AUTONOMA BARCELONA,UNITAT QUIM ORGAN,E-08193 BARCELONA,SPAIN

来源：

TETRAHEDRON | 1992年 / 48卷 / 25期

关键词：

D O I：

10.1016/S0040-4020(01)89031-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conventional ionic bromination of electron-poor olefins, 2-(1-hydroxyalkyl)- and 2-(1-alkoxyalkyl)propenoates, 2b-d, and methyl (E)-2-(1-hydroxyethyl)-2-butenoate, 3a, proceeds with yields higher than 80%. Treatment of (E)-3-bromo-2-[1-[(2-methoxyethoxy)methoxy]butyl]propenoic acid, 16, with two equivalents of strong bases, reaction related with a possible hydroxyfimbrolide and bromobeckerelide synthesis, resulted in the halogen-metal exchange reaction affording the acrylic acid 18, presumably through the generation of dianion 19.

引用

页码：5347 / 5358

页数：12

共 37 条

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