Summary
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1.
The reactions of 16β-bromo-3β,17α-dihydroxypregn-5-en-20-dione (III) and its 3,17-diacetate (IV) with aniline have been studied. The reaction of (III) with aniline leads to the formation of the 20-anil of 16α,17α-epoxypregnenolone (V) and the reaction of (IV) with aniline to the formation of 3-acetoxy-16α-(N-acetylanilino)-17α-hydroxypregn-5-en-20-one (IX).
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2.
The hydrolysis of the diacetate (IX) with potassium carbonate in aqueous methanol has been studied. The hydrolysis is accompanied by D-homoisomerization with the formation of 16α-anilino-3β,17α-dihydroxy-17β-methyl-D-homoandrost-5-en-17a-one.
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3.
The structures and configurations of the compounds obtained (V, VI, VII, IX, X, and XI) have been shown by a series of chemical transformations and by physicochemical methods.
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Additional information
S. Ordzhonikidze All-Union Scientific-Research Institute of Pharmaceutical Chemistry. M. M. Shemyakin Institute of the Chemistry of Natural Compounds, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 509–514, July–August, 1971.
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Suvorov, N.N., Frangulyan, G.A., Sadovskaya, V.L. et al. Steroids XLIV. Synthesis and D-homoisomerization of 3β-acetoxy-6α-(N-acetylanilino)-17α-hydroxypregn-5-en-20-one. Chem Nat Compd 7, 481–485 (1971). https://doi.org/10.1007/BF00564743
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DOI: https://doi.org/10.1007/BF00564743