The foci of this research extend to total synthesis and methodology development. Specific molecular targets include the TNF-alpha antagonist vinigrol, the potent insecticidal alkaloid haplophytine, the octacyclic polyterpenoid octacyclononaprenol, the plant hormone precursor 3alpha-hydroxy-ent-kaurene and the potent steroidal contraceptive agent desogestrel. Among the topics of study in new methodology are enantioselective catalytic phase transfer alkylation of enolates, design and application of chiral super Lewis acids as catalysts for enantioselective synthesis, new oxazaborolidine catalysts for the enantioselective reduction of carbonyl groups, a new process for the synthesis of chiral alpha-stannyl- and alpha-lithio-carbinols, and new stereospecific methods for the synthesis of olefins by fragment coupling and the application of theses products to the synthesis of complex polycyclic structures by cation-olefin cyclization. With this renewal award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Elias J. Corey of the Department of Chemistry and Chemical Biology at Harvard University. Professor Corey will focus his work on the development of multistep synthetic pathways to complex, bioactive organic compounds and on the discovery of new and general methods for the construction of organic molecules.
