Synthesis of C-5 Substituted Tubercidin Derivatives.
Annual progress rept. 1 Feb 78-31 Jan 79,
CALIFORNIA UNIV DAVIS
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Methodology for the synthesis of tubercidin derivatives substituted by carbon chains at the C-5 position has been developed. 5-Mercuritubercidin, prepared by reaction of tubercidin with mercuric acetate in water, undergoes coupling to olefins when treated with lithium palladium chloride in either methanol or N,N-dimethylformamide. In this way 5-1-methoxyethly tubercidin was prepared from ethylene, 5-2-cyanoethenyltubercidin from acrylonitrile, 5-2-carboxamido-ethenyltubercidin from acrylamide, and 5-2-methoxycarbonylethenyl tubercidin from methyl acrylate. Various synthetic transformations of these tubercidin derivatives were investigated.