Synthesis of (+)-Voglibose

Abstract

A concise asymmetric synthesis of voglibose, a natural product derivative and an alpha-glucosidase inhibitor with antihyperglycemic activity, was produced from an O-arylated lactic acid derivative in only seven steps. This approach was based on an oxidative phenol dearomatization process promoted by a hypervalent iodine reagent, a chiral auxiliary serving as a protecting group and allowing the asymmetric formation of the target, and a key hydrolysis leading to the formation of several contiguous stereocenters and removal of the chiral auxiliary.