RUI: A Cyclopropane Fragmentation Approach to Heterocycle Synthesis

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This project aims to develop a unified route to the synthesis of heterocycles with different ring size and heteroatom. The chemistry proposed relies on the nucleophilicity of cyclopropanols, underutilized but competent nucleophiles, cyclizing on an in-situ generated iminum or oxonium species. This condensation/rearrangement strategy results in a ring expansion, and promises high levels of stereocontrol. After reaction optimization in the oxepane system, this heterocycle formation strategy will be extended to the synthesis of tetrahydropyrans, piperidines, and azepines. The utility of this methodology will be showcased in the synthesis of spectalinine A and a formal synthesis of isolaurepinnacin.With the support of this RUI award from the Organic and Macromolecular Chemistry Program, Professor Kevin P. Minbiole, of the Department of Chemistry at James Madison University, is exploring a new approach for the synthesis of heterocycles, molecular rings containing at least one atom that is not carbon. Heterocyclic compounds constitute the backbone of innumerable compounds of biomedical importance. This project aims to develop a unified route to the synthesis of heterocycles with different ring sizes and heteroatoms. As new methodologies are developed, their utility will be illustrated through their application in the synthesis of representative naturally occurring compounds. All work in this program will be carried out by undergraduates, including students from less research-active regional colleges.