NEW METHODOLOGY FOR ORGANIC SYNTHESIS

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This project involves the development of a number of new reactions and concepts for organic synthesis. These will include studies of the potential for "aqueous" pentadienyl anion chemistry and the asymmetric induction of an arene chromium group in the Diels-Alder reaction. Total syntheses of vitamin D derivatives, including receptor ligands, and taxusin will be undertaken. New organosilicon methodology will be developed involving asymmetric induction in Claisen rearrangements by the TMS group. Internal activation of allylsilanes will be studied. The oxidative fragmentation of silanes and the oxidative free-radical addition to allylsilanes will be investigated. Finally, both photodecarbonylation and solvolysis reactions will be applied to leukotriene synthesis. Although the primary goal is to learn all that we can about the reactions in question, these new reactions will be investigated in the context of synthetic problems of current interest such as vitamin D metabolites, affinity ligands for the vitamin D receptor, taxusin, precursors for taxol antibodies, quinine, ajmalicine, recifeiolide, X-14547A, tetronomycin, zoapatanol, pinidine, forskolin, and leukotrienes.