Natural product inspired synthetic methods

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The proposed research program involves three primary areas of investigation. One of these features the cobalt catalyzed aerobic oxidations of 5-hydroxy pentenes for THF synthesis, the application of these oxidations in total synthesis, expanding reaction scope and improving catalyst performance. Recent highlights in this area from our lab include the asymmetric total syntheses of the natural products bullatacin and aplysiallene. A major synthetic target described in the proposal is amphidinolide C. A second area of investigation involves the discovery of new reactions of donor-acceptor cyclopropanes and their application in total synthesis. This work has provided new syntheses of pyrroles, indoles, indolizines and other useful heterocycles, and was a key reaction in a recent total synthesis of goniomitine. Ongoing investigations will look for additional annelation partners and cyclopropane motifs, as well as targets for total synthesis. A third major area of research involves collaborative work on silole based materials. Our group performs the syntheses and further studies, particularly electrogenerated chemiluminesence and photo voltaic responses, are measured in the Ding and Semenikhin groups.