Total Synthesis of Phyllanemblinin B

Abstract

A total synthesis was developed of phyllanemblinin B, a natural ellagitannin containing 1-O-galloyl and 2,4-O-hexahydroxydiphenoyl groups on a d-glucose scaffold. The use of a μ-hydroxo copper(II) complex resulted in a completely stereoselective oxidative coupling of the galloyl groups on the open-chain glucose moiety and facilitated the first total synthesis of phyllanemblinin B.