SYNTHESIS OF MACROLIDES, TETRAMIC ACIDS, AND VITAMINS

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This program continues investigations in synthetic and mechanistic organic chemistry. These studies are of general medicinal interest relating to substances which are antifungal, antineoplastic, and antibacterial agents and vitamins. Several of the substances of this type include carbomycin B, tirandamycin, streptolydigin, pyrenophorin, vermiculin among the antibiotics and vitamins E and K which will serve as models for mechanistic studies. A major facet of the program involves the use of sigmatropic rearrangments to control stereochemistry in the tirandamycin, streptolydigin, and vitamin work. Palladium-mediated, ambient temperature coupling reactions developed in this laboratory will be applied in the synthetic program related to carbomycin B, pyrenophorin, and vermiculin.