Synthesis of 7α-methyl-19-nortestosterone 6-chloro(methoxy) nicotinates
Abstract
New 7α- and 7β-methyl-19-nortestosterone derivatives containing 6-chloro- or 6-methoxynicotinic acids fragments at C-17 have been prepared. The key intermediate, 19-nor-6-dehydrotestosterone acetate, was synthesized from diosgenin. A copper(I) chloride catalyzed 1,6-conjugate addition of methylmagnesium iodide to 19-nor-6-dehydrotestosterone acetate led to a mixture of 17β-acetoxy-7α-methylestr-4-еn-3-one as a major product and their 7β-isomer. Methanolysis and then acylation of made compounds with 6-chloronicotinoyl chloride or 6-methoxynicotinoyl chloride gave the corresponding target 17β-(6-chloronicotinoyloxy)-7α-methylestr-4-en-3-one, 17β-(6-chloronicotinoyloxy)-7β-methylestr-4-en-3-one and 17β-(6-methoxynicotinoyloxy)-7α-methylestr-4-en-3-one.
About the Authors
M. N. Kauhanka
Institute of Bioorganic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Ju. G. Charnou
Institute of Bioorganic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Zh. N. Kashkan
Institute of Bioorganic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
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