Chiral Sulfoxides in Asymmetric Synthesis: Enantioselective Synthesis of the Lactonic Moiety of (+)-Compactin and (+)-Mevinolin. Application to a Compactin Analogue

The lactonic part of (+)-compactin and (+)-mevinolin as well as a compactin analogue were synthesized in an enantioselective way from a beta,delta-diketo sulfoxide easily obtained by the reaction of the trianion of methyl 3,5-dioxohexanoate with (-)-menthyl (S)-p-toluenesulfinate. The main reaction was the two-step stereoselective reduction of beta,delta-diketosulfoxide without any protective group.