Studies directed toward the synthesis of rhizopodin: stereoselective synthesis of the C1–C15 fragment

Abstract

A stereoselective synthesis of the C1–C15 fragment of a G-actin binding natural macrodiolide, rhizopodin was achieved using, as key steps, highly stereoselective acetate aldol reactions to build the C1–C7 fragment, one pot oxazole synthesis and an asymmetric Keck allylation reaction to build the C8–C15 fragment and finally, a Stille reaction to couple both the fragments.