SYNTHESIS OF 19-NORTESTOSTERONE PROTIONATE FROM TESTOSTERONE PROTIONATE
Abstract
Synthesis of androgen 19-nortestosterones via new synthetic scheme has been achieved. The synthesis commenced with commercially available testosterone propionate which was transformed to 3β-acetoxy-17β-propyonyloxy-androst-5-en. Hypobromous acid was added to the 5(6)-double bond of the latter compound leading to 3-acetate 17-propionate 5-bromo-5αandrostane-3β,6β,17β-triol that was oxidized by lead tetraacetate giving the 3-acetate 17-propionate 5-bromo-6β,19-oxido5α-androstan-3β,17β-diol. Selective hydrolysis of the acetate group of the latter provided 17-propionate 5-bromo-6β,19-oxido5α-androstan-3β,17β-diol. Oxidation of the 3β-hydroxy group of the obtained compound by chromic acid followed by reduction of the resulting 3-keto group by zinc dust in methylethylketone gave 19-hydroxytestosterone-17-propionate. Oxidation of the resulting 19-hydroxysteroid by chromic acid and subsequent decarboxylation of 19-carboxylic acid by its heating in a mixture of pyridine and benzene led to the target 19-nortestosterone propionate.
About the Authors
M. U. Kauhanka
Institute of Bioorganic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
V. I. Dolgopalets
Institute of Bioorganic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Yu. G. Charnou
Institute of Bioorganic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
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