Chiral sulfoxides in asymmetric synthesis: Enantioselective synthesis of the lactonic moiety of (+)-compactin and (+)-mevinolin. Application to a compactin analogue

Article abstract of DOI:10.1021/jo00129a018

The lactonic part of (+)-compactin and (+)-mevinolin as well as a compactin analogue were synthesized in an enantioselective way from a β,δ-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 β,δ-diketo sulfoxide without any protective group.