Easy Access to 5-Alkyl-4-bromo-2(5H)-furanones: Synthesis of a Fimbrolide, an Acetoxyfimbrolide, and Bromobeckerelide

Pedro De March, Josep Font, Antonio Gracia, Zheng Qingying

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Abstract

Treatment of y-monosubstituted allenic esters with iV-bromosuccinimide in water yields 5-alkyl-4-bromo-2(5.H)-furanones, that can be transformed into 5-alkylidene-4-bromo-2(5H)-furanones in good overall yields. Starting with a simple allenic ester these transformations have been applied to a new synthesis of fimbrolide (la), acetoxyfimbrolide (lc), and bromobeckerelide (2a). © 1995, American Chemical Society. All rights reserved.
Original languageEnglish
Pages (from-to)1814-1822
JournalJournal of Organic Chemistry
Volume60
Issue number6
DOIs
Publication statusPublished - 1 Mar 1995

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