Synthesis of (E)-4-bromo-3-methoxybut-3-en-2-one, the key fragment in the polyhydroxylated chain common to oscillariolide and phormidolides A-C

Abstract

The terminal bromomethoxydiene (BMD) moiety of the polyhydroxylated chain present in phormidolides and oscillariolides has been synthesized for first time. Several strategies for the stereoselective synthesis of the 4-bromo-3-methoxybut-3-en-2-ones are described. Furthermore, a preliminary study to successfully introduce this fragment within the polyol chain and introduction of the fatty acid allowed corroborate the end structure of the polyol.