Halogenated Cyclic Allylic Cations in 4+3 Cycloadditions

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The focus of this research is the development of 4 + 3 cycloadditon chemistry and its use in the preparation of natural products. The intermediates to be prepared are halogenated, principally brominated, cyclic oxyallylic and allylic cations. Cycloadditons followed by quasi-Favorskii rearrangement leading to the preparation of synthons for cyclobutadiene 4 + 2 cycloadditon reactions will be a key strategy of the project. Synthetic targets which will be approached include poduran, sulcatine G, sterpurene, spatol and isocomene. The research offers a sound project for the training of graduate students. With this Renewal award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Michael Harmata of the Department of Chemistry of the University of Missouri-Columbia. Professor Harmata will focus his work on the preparation of complex organic compounds using 4 + 3 cycloaddition chemistry. The approach could have broad impacts in the pharmaceutical and agricultural industries.