Synthesis of Heterocyclic Natural Products

This research program deals with the stereospecific total synthesis of several complex naturally-occurring molecules having biological and/or structural significance. In particular, emphasis will be placed upon producing and refining methodology having potentially broad applicability which will be of practical use to both organic and medicinal chemists involved in synthesis of chemotherapeutic agents. Work has been initiated on total syntheses of some of the challenging, structurally unique polycyclic marine bryozoan alkaloids of the chartelline/chartellamide/securamine group and these studies will be continued during the requested grant period. Specifically, total syntheses of chartelline A and securine A/securamine A will be completed. In addition, studies are nearing completion on a short enantioselective total synthesis of the unusual Securinega alkaloid secu?amamine A via a novel tandem multistep process to construct the unique tetracyclic ring system of the natural product.

With this award, the Organic and Macromolecular Chemistry Program of NSF is supporting the research of Professor Steven M. Weinreb of the Department of Chemistry at Penn State University. Professor Weinreb's research efforts revolve primarily around the development of efficient new methodology for the synthesis of heterocyclic organic compounds, and applications of this chemistry to the synthesis of important structurally complex natural products. Successful development of the methodology will have particular impact on synthesis of intermediates in the pharmaceutical and agricultural industries.