Short, Enantioselective Synthesis of Mevalonic Acid

Abstract

A new enantioselective synthesis of mevalonic acid that is short, flexible, scalable to gram amounts, and uses readily available starting materials is reported. Enantioselective homoallylic epoxidation of isoprenol followed by enantiomeric enrichment gave the key epoxide intermediate. Further reactions led to either racemic mevalonic acid in 74% yield over two steps or the individual (R)- or (S)-enantiomer on a gram scale in 51% overall yield and ≥99% ee over five linear steps.