Kinetic Resolution of Diols via Etherification Catalyzed by a Chiral Phosphoric Acid: Concise Synthesis of (+)-SacidumlignanD

Abstract

A kinetic resolution of a diol via etherification catalyzed by a chiral phosphoric acid was developed and applied in the concise total synthesis of (+)-sacidumlignan D, the antipode of natural sacidumlignanD. A zinc-mediated crotylation of a diarylketone and subsequent lactonization quickly established the carbon framework of this class of tetrahydrofuran lignans. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.