With this award, the Synthetic Organic Program will support the research of Dr. Eric J. Enholm of the Department of Chemistry at the University of Florida. Dr. Enholm's research is in the broad area of the development of new synthetic methodology which can then be applied to a variety of total syntheses. The specific goals of the proposed studies are to study synthetic applications of various one-electron coupling reactions of two unsaturated centers which lead to carbon-carbon bond formation. Dr. Enholm will focus his efforts on carbonyl-alkene cyclization, the preparation of carbocycles from carbohydrates, the coupling of dicarbonyl compounds and a newly developed free radical coupling reaction mediated by tributyltin hydride. Targets projected for eventual total synthesis include the natural products anguidine, tricotriol and tylonide hemiacetal.