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
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.
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页码:5347 / 5358
页数:12
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