This research involves the use of metal stabilized vinylcarbenoids as reactive intermediates in organic synthesis with three specific aims. First is the development of asymmetric synthesis with vinyl carbenoids using (-)-pantolactone and related systems as inexpensive chiral auxilaries. Second is the synthesis of phorbol analogues using the tandem cyclopropanation/Cope rearrangement sequence. The third area is the study of novel annulation reactions based on preliminary observations which have shown unusual reactivity at the vinyl terminus of monosubstituted vinylcarbenoids containing an electron withdrawing group. %%% With this award the Synthetic Organic Program of the Chemistry Division will support the research of Dr. Huw M.L. Davies of the Department of Chemistry at Wake Forest University. The research involves the use of metal stabilized vinylcarbenoids as reactive intermediates in organic synthesis. These intriguing and fascinating species will be used to development asymmetric synthetic methodology. Their utility will be demonstrated in the synthesis of several natural products or analogues.
