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.
|Journal||Journal of Organic Chemistry|
|Publication status||Published - 1 Mar 1995|