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.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
2R01GM029259-05
Application #
3276821
Study Section
Medicinal Chemistry Study Section (MCHA)
Project Start
1980-09-01
Project End
1990-08-31
Budget Start
1986-09-15
Budget End
1987-08-31
Support Year
5
Fiscal Year
1986
Total Cost
Indirect Cost
Name
New York University
Department
Type
Schools of Arts and Sciences
DUNS #
004514360
City
New York
State
NY
Country
United States
Zip Code
10012
Wilson, S R; Cui, W L (1990) Applications of simulated annealing to peptides. Biopolymers 29:225-35
Spector, A; Wilson, S R; Zucker, P A et al. (1989) The synthesis of glutathione peroxidase analogs. Lens Eye Toxic Res 6:773-80