Diastereoselective synthesis of alpha -tocopherol : a new concept for the formation of chromanols

Abstract

A diastereoselective synthesis of alpha-tocopherol (93% de) was achieved via two key steps, (i) a highly diastereoselective Shi epoxidn. of trisubstituted alkene I and (ii) an acid supported, "anti-Baldwin" epoxide ring opening under inversion of configuration leading to the 6-membered chromanol ring