Synthesis of Carbocyclic and Heterocyclic Natural Products

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9316939 White The focus of this research is the discovery of new synthetic methods and their application to the synthesis of certain carbocyclic and heterocyclic compounds of natural origin. Five natural products are identified for the purpose of defining the specific goals of the project. They fall into two groups, one consisting of a set for which bond reorganization involving a cyclobutane is the focal step, and another in which elaboration of a heterocyclic subunit plays a pivotal role. The first group contains rubratoxin B, verrucarol, and huperzine A. The second group contains the alkaloids cylindrospermopsin and koumine. The major emphasis in all of the syntheses is the ability to complete efficient routes to structures containing a high degree of complexity. %%% With this award, the Synthetic Organic Program is supporting the research of Dr. James D. White of the Department of Chemistry at Oregon State University. Professor White will focus his work on the discovery of new synthetic methods and their application to the synthesis of certain carbocyclic and heterocyclic compounds of natural origins. The molecular architecture of the designated target compounds presents a significant challenge to contemporary methods of synthesis which will be addressed by exploring unconventional and, in several instances, unprecedented approaches to their construction. ***