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Natural Product Synthesis as an Entry to Methodological and Biological Studies

Speaker: Paul Floreancig, PhD, Professor and Director of Graduate Studies, Department of Chemistry, University of Pittsburgh Location: 402 N Blackford St. Indianapolis, IN 46202 LD 010

This presentation will describe the advancement of two transformations that were designed for the completion of the synthesis of the natural product leucascandrolide A into new research directions. The first method utilizes Re2O7-mediated allylic alcohol transpositions to initiate new complexity-generating processes, including cyclizations, cascade processes, and dehydrative couplings. The method is highlighted by its application to the synthesis of the spliceosome inhibitor herboxidiene and an analog that provides information on the biologically relevant conformation of the natural product. The other method employs DDQ-mediated oxidative carbon–hydrogen bond functionalization as a prelude to intra- and intermolecular carbon–carbon and carbon–oxygen bond formation. This method provided the inspiration for multiple new heterocycle syntheses and an intensive computational study, while also serving as the basis for the syntheses of the natural products neopeltolide, clavosolide A, bistramide A, and divergolides E and H. Select structure-activity relationship studies will also be discussed.

Host: Laulhé