The focus of this research is the development of new methods for the stereoselective formation of a carbon-heteroatom and a carbon-carbon bond in a single process. The methodology will exploit diazo compounds that possess an alpha-electron withdrawing group as one carbon dipoles in ring forming reactions. The preparation of tetrahydrofurans, tetrahydropyrans, oxetanes, azacyclics and carbocycles will be carried out and the new methodology will be showcased by the preparation of shodamycin and the E-ring of lonomycin. Both of these systems show important biological activity. With this award, the Synthetic Organic Program is supporting the research of Dr. Steven R. Angle of the Department of Chemistry at the University of California, Riverside. Professor Angle will focus his work on developing new methods for ring-forming reactions. The products of these reactions are oxygen heterocycles, nitrogen heterocycles and carbocycles, all of which can occur in compounds having interesting and important biological properties.
