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.