Synthesis of the macrolactone core of the revised structure of palmerolide C

Abstract

Abstract Synthetic efforts towards the total synthesis of the revised structure of marine macrolide palmerolide C is reported. Synthesis of the triol unit present in the C8,C9, C10 positions was achieved from D-ribose while Johnson orthoester rearrangement and a Wittig reaction were used to construct the C1-C7 component of the macrolactone. The key macrolactone unit was assembled using intermolecular Stille coupling reaction and Yamaguchi lactonization.