EASY ACCESS TO 5-ALKYL-4-BROMO-2(5H)-FURANONES - SYNTHESIS OF A FIMBROLIDE, AN ACETOXYFIMBROLIDE, AND BROMOBECKERELIDE

Authors
DEMARCH P FONT J GRACIA A ZHENG QY
Citation
P. Demarch et al., EASY ACCESS TO 5-ALKYL-4-BROMO-2(5H)-FURANONES - SYNTHESIS OF A FIMBROLIDE, AN ACETOXYFIMBROLIDE, AND BROMOBECKERELIDE, Journal of organic chemistry, 60(6), 1995, pp. 1814-1822
Citations number
44
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
60
Issue
6
Year of publication
1995
Pages
1814 - 1822
Database
ISI
SICI code
0022-3263(1995)60:6<1814:EAT5-S>2.0.ZU;2-X
Abstract
Treatment of gamma-monosubstituted allenic esters with N-bromosuccinim ide in water yields 5-alkyl-4-bromo-2(5H)-furanones, that can be trans formed into 5-alkylidene-4-bromo-2(5H)-furanones in good overall yield s. Starting with a simple allenic ester these transformations have bee n applied to a new synthesis of fimbrolide (1a), acetoxyfimbrolide (1c ), and bromobeckerelide (2a).