SYNTHESIS OF INTERMEDIATES FOR THE LACTONE MOIETY OF MEVINIC ACIDS VIA TELLURIUM CHEMISTRY

Treatment of p-toluenesulfonates of epoxides of specific primary allyl ic alcohols with telluride ion, prepared in situ by reduction of relat ively nontoxic elemental tellurium, installs the two key secondary alc ohol functions that occur in the lactone part of the cholesterol-lower ing drugs, compactin, mevinolin, and lovastatin. Since the epoxides of the primary allylic alcohol starting materials can be synthesized in optically active form by the Sharpless-Katsuki asymmetric epoxidation (SAE) process, the stereospecific telluride transposition can give opt ically active secondary allylic alcohols configured for maximum inhibi tion of cholesterol function.