Chiral Vinyloxiranes as Synthetic Intermediates

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The Organic Synthesis Program is funding a continuation of the research of Dr. James A. Marshall. Dr. Marshall will continue his development of new ways to control the stereochemistry in the synthesis of complex systems. These will provide the new tools required by the increasing complexity of the compounds needed by our agriculture and industry. The research will explore the scope of reactions in which nonracemic vinyloxiranes serve as key intermediates for the synthesis of subunits found in various polypropionate and related natural products. The experiments are designed to reveal intrinsic steric preferences and explore the role of directing groups in these reactions. A variety of nucleophilic reagents will be tested including nonracemic cuprates and allylmetallic compounds. By the proper selection of double bond geometry, epoxide stereochemistry and reagent sterochemistry it should be possible to exercise considerable control over the formation of multiple stereocenters. Methodology will also be explored for transforming the products of the foregoing reactions into natural products and analogs with potential antitumor, antibiotic, and immunosuppressive properties.