The Synthetic Organic Chemistry Program will be supporting the research of Dr. Steven M. Weinreb of the Department of Chemistry at Pennsylvania State University. Dr. Weinreb will be developing new methods of synthesizing heterocyles, an important type of chemical structure found in many complex structures. These are found in many of the substances used in modern agriculture and medicine. Synthetic methodology and natural product total synthesis based upon N-sulfinyl dienophile Diels-Alder cycloadditions will be pursued. The methodology will specifically be applied to synthesis of the Nuphar alkaloid 7-epi-anhydronupharidine. In addition, an intramolecular version of the procedure will be utilized for the stereoselective synthesis of vicinal diamines in a new total synthesis of capreomycidine. This is a component of the antibiotics capreomycine and the tuberactinomycidines, and will be used in an efficient synthesis of streptolidine, which is a member of the streptothricin antibiotics. A stereoselective synthesis of the vitamin biotin will also be developed using this Diels-Alder based methodology. A new procedure for synthesis of vicinal diamines will be investigated via metallation of cyclic bis-imines. A novel variation of the Heck reaction will be studied in order to efficiently synthesize saturated nitrogen heterocycles. Moreover, nickel metallacycles derived from alkynes and carbon dioxide will be investigated in order to develop some generally useful synthetic methodology. These metallacycles will be utilized as beta-acylvinyl anions and their reactions with several types of electrophiles will be tested.
