Studies of New Reactivity for Efficient Strategies Toward Bioactive Natural Products

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With this award, the Chemical Synthesis Program is funding Professor David R. Williams of the Department of Chemistry at Indiana University to explore the behavior of electrocyclization reactions of pentadienyl carbanions. The proposed methodologies will elucidate reactivity leading to electrocyclic ring closures which provide efficient access to unique ring systems. Initial studies will generate substrates for investigations of tandem reactions of stereoselective rhodium-catalyzed hydroacylations and iron-catalyzed Pauson-Khand processes. These transformations target the efficient molecular assembly of architectures that are difficult to access or as yet unattained by the prior art. The inclusion of these molecular frameworks in naturally-occurring antitumor antibiotics and recently discovered marine natural products provides additional significance for the proposed studies. Moreover, these studies will contribute a better understanding of the reactivity, scope, and mechanisms of the key proposed reactions. Successful development of the proposed research plan will impact the need for new methodologies and strategies for chemical synthesis in the pharmaceutical, chemical, and agricultural industries. The project will provide training in sophisticated modern synthesis toward biologically relevant targets to both undergraduate and graduate students, including underrepresented minorities in a supportive environment emphasizing scholarship and creativity.