DESCRIPTION: The principal investigator states that the program to continue to evaluate the synthetic properties of chiral, non-racemic bicyclic lactams is presented. He notes that the lactams, derived from optically active amino alcohols (by reduction of amino acids) and 3- or 4-ketocarboxylic acids provide a chiral template upon which to perform an unusual number of synthetic reactions: alkylations, additions, cycloadditions (photo, thermal, acid-catalyzed), reductions, oxidations, and others. He further indicates that the products of these chemical reactions lead to a plethora of enantiomerically pure quaternary carbon compounds, many of which are natural products with important biological activity. It is noted that the present proposal will extend these studies to contiguous chiral centers, chiral pyrrolidines and piperidines. The latter are said to be important core systems in a number of biologically active compounds.