The diospongins and ezomycins are plant- and bacterial-derived natural products, respectively, which have been popular targets for synthesis due to their intruguing but simple structures and potential biological activity.  Long-term goals of our research program include the development of efficient, enantioselective syntheses of these natural products using chiral pool strategies.   We will report our most recent results from attempts to forge the diospongin sterochemical array starting from commercially available carbohydrates and proceeding via modern metal-catalyzed couplings.  We will also communicate our progress toward the synthesis of the ezomycin ring system starting from a glucuronic acid derivative; our strategy focuses on minimization of protecting groups and leveraging of modern bond-forming reactions to preserve step economy.

Progress toward the synthesis of the diospongins and related natural products

254th National Meeting (2017)

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