Towards the synthesis of amphidinolide B. An intramolecular Stille coupling approach

Abstract

A synthetic approach towards the cytotoxic polyene polyol macrolide amphidinolide B ( 1), based on elaboration of the C 1C 13 carboxylic acid 4 and the C 14C 25 alcohol 3 units, their esterification to the iodostannyl ester 2, and an intramolecular Stille sp 2– sp 2 coupling reaction, is described. In spite of adequate precedent and model experiments, circumstances conspired and the aforementioned coupling reaction was not realised in this case.