With the support of the Organic and Macromolecular Chemistry Program, Professor Steven M. Weinreb, of the Department of Chemistry at Pennsylvania State University, University Park, is carrying out the stereoselective total synthesis of several complex naturally-occurring molecules of biological significance, complemented by the development of new and practical methods for organic synthesis. An approach to the total synthesis of the hepatotoxic alkaloid cylindrospermopsin uses as a pivotal step Professor Weinreb's N-sulfinyl dienophile Diels-Alder methodology. Several structurally unique polycyclic marine bryozoan alkaloids of the chartelline/securamine class will also be synthesized. The total synthesis of the recently isolated novel pentacyclic indole alkaloid tronocarpine will utilize the unique chemistry of 1-hydroxyindoles. New methods of chemical synthesis will be investigated, including a simple alternative to the Eschenmoser coupling reaction for preparing vinylogous amides and carbamates, and the use of N-sulfinyl compounds as reagents for the formation of glycosidic and N-glycosidic bonds.
Construction of the often-complex molecules which display desirable biological or pharmaceutical activity requires the development of new and sophisticated methods for the synthesis of organic molecules. As new methods are developed, they ultimately must be tested and proven effective through their application to real synthetic problems. Such testing also provides training in the thought processes and practice of organic synthesis, vital to the educational development of students who will become the next generation of practicing organic chemists. With the support of the Organic and Macromolecular Chemistry Program, Professor Steven M. Weinreb, of the Department of Chemistry at Pennsylvania State University, University Park, is exploring the development of new and practical methods for organic synthesis and applying them to the total synthesis of several complex naturally-occurring molecules of biological significance.
