APPROACHES TO CHIRAL QUATERNARY CARBON COMPOUNDS

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Studies are in progress to continue evaluation of an asymmetric synthesis of quaternary carbon compounds which have shown considerable potential in its first two years of support. By use of chiral bicyclic lactams, readily prepared from L-valinol and alpha or gamma-ketoacids, an asymmetric total synthesis of (+)- mesembrine, (-)grandisol, and (-)-cuparenone have been accomplished. We now wish to further extend the scope and methodology of this powerful technique to alkaloids of the aspidosperma and vinca class, triquinanes, abscisic acids-potent plant growth regulators, trisporic acids-fungal regulators, halenaquinol-anti-microbials, vinylcyclopropanes, pyrethroids, cyclopropylamines-anti-depressents, cyclobutanes-analegesics, and a host of interesting, chiral, non-racemic compounds of medicinal value. In addition, mechanistic and structural studies will be carried out concurrently to assess the full potential of these bicyclic lactams.