Short and stereoselective synthesis of α-methylene-β-hydroxy-γ-butyrolactone diastereomers

Abstract

A short synthetic approach allowed the preparation, in two steps, of (3S,4R)- and (3R,4R)-2- methylene-3-hydroxy-4-(hydroxymethyl)-γ-butyrolactones from 2,3-O-(3-pentylidene)-D-glyceraldehyde, with overall yields of 32 % and 9 %, respectively. The structure of these γ-butyrolactones was revised by experimental and theoretical investigations.