Enantioselective Synthesis of Apoptolidinone:Exploiting the Versatility of Thiazolidinethione Chiral Auxiliaries

摘要

Apoptolidin A(1)(Figure 1)is a potent,selective mediator of apoptosis in E1A transformed rat glia cells.Khosla has shown that apoptolidin induces cell death by inhibiting the mitochondria! F_0F_1-ATPase.As a result of its remarkably selective effects on cancer cells,apoptolidin A shows great potential for the treatment of cancer.The interesting chemical structure,combined with its appealing biological properties,has made apoptolidin A an attractive target for synthesis.Since the isolation and structure elucidation of apoptolidin A,two total syntheses,two syntheses of apoptoli-dinone,several partial syntheses,as well as a number of synthetic modifications have been reported.