Asymmetric Synthesis of Biologically Active Materials

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DESCRIPTION: (Applicant's Description) Our principle goal during the tenure of this grant will be the development of new catalyzed organic reactions for the stereospecific assemblage of C-C bond with broad, applications to the synthesis of a variety of target compounds possessing pharmacological activity. The reaction technology under development is specifically designed to address fundamental C-C bond forming reactions that are generally applicable to complex molecule synthesis and the preparation of important chemical building blocks in the context of industrial or medicinal chemistry synthesis activities. Catalyzed asymmetric acyl chloride-aldehyde cyclocondensations developed in our laboratories are further developed as versatile reaction technology for asymmetric organic synthesis. This methodology will be refined and developed in the context of the total synthesis of naturally occurring materials that express potent anticancer and antiviral activities, including amphidinolide B, rhazinilam, and motuporin. Moreover, a family of unique optically active Al(III)-based Lewis acids will be developed as bifunctional Lewis acidic-Lewis basic catalysts with applications to a variety of asymmetric C-C bond constructions. An economical and operationally simple synthesis of highly enantiomerically enriched beta-amino acids is also exploited in an efficient approach to the synthesis of beta-peptides and the preparation of cyclic beta-peptide structures designed to function as integrin receptor antagonists.