Natural Product Inspired Synthetic Methods

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The Pagenkopf group has been engaged in four primary areas of research within organic synthesis. We plan to continue the discovery of new reactions of donor-acceptor cyclopropanes and exploring applications in natural product synthesis. A key natural product we plan to prepare is the anti-cancer compound streptorubin B, and the approach features a new strategy that utilizes a cyclopropane incorporated into a macrocycle to assemble one of the pyrroles. The successful outcome could be broadly applicable to the synthesis of analogs and other members of the prodigiosin family. Secondly, the group has been engaged in the development of new catalysts for the synthesis of tetrahydrofurans (THF’s) from hydroxy olefins under green conditions by utilizing air as the stoichiometric oxidant. Some key synthetic targets under investigation include the biologically active natural products amphidinolide C and biselide A, both of which show impressive anti-cancer activity. And third, we have been engaged in the synthesis of novel siloles and exploration of their properties. Through structural modification by chemical synthesis new materials with useful functional properties are being developed. And forth, we have recently begun exploring the reactions of a new class of donor-acceptor cyclobutanes, and plans to discover new reactions are described. The importance of synthetic chemistry to materials science and the pharmaceutical industry is well understood as synthetic chemistry is a fundamental aspect of these industries, which are important contributors to the Canadian economy. New, useful synthetic methods are required to expand the tool-box of chemical reactions available to the synthetic, medicinal or process chemist. In this proposal, plans have been put forth to develop new chemical transformations which will assist the chemical community in their synthetic endeavors. In addition, an extended knowledge of chemical reactivity will be gained through natural product synthesis. These efforts provide excellent training for careers in the pharmaceutical and related industries. The silole based materials being explored have the potential to directly impact biomedical and environmental chemistry by, for example, aiding in the early detection of disease through improving sensitivity over some existing methods.