Steroids p. 149 - 160 (1981)
Update date:2022-08-03
Topics:
Numazawa, Mitsuteru
Osawa, Yoshio
A novel synthesis of 16α-hydroxy-4-androstene-3,17-dione (3), 16α-hydroxy-4-androstene-3,6,17-trione (4), 17β-amino-5-androsten-3β-ol (10) and 17β-amino-4-androsten-3-one (14) is described. 16α-Bromoacetoxy-4-androstene-3,17-dione (5), 16α-bromoacetoxy-4-androstene-3,6,17-trione (6) and 17β-bromoacetylamino-4-androsten-3-one (15) were synthesized as potentially selective irreversible inhibitors of androgen aromatases. 16α-Bromo-4-androstene-3,17-dione (1) and 16α-bromo-4-androstene-3,6,17-trione (2) were converted to compounds 3 and 4 in 80-90percent yield by controlled stereospecific hydrolysis using sodium hydroxide in aqueous pyridine.Reductive amination of 3β-hydroxy-5-androsten-17-one and 3-methoxy-3,5-androstadien-17-one (11) using ammonium acetate and sodium cyanohydridoborate (NaBH3CN) and a subsequent treatment with acid gave the amines 10 and 14, respectively, as a salt.The corresponding 17-imino compounds 9 and 13 were also isolated from the reaction mixtures when methanol was used as a solvent for the reaction.The 16α-hydroxyl compounds 3 and 4 and the 17β-amino compound 14 were converted to the corresponding bromoacetyl derivatives, 5, 6, and 15, with bromoacetic acid and N,N'-dicyclohexylcarbodiimide.
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Doi:10.1007/BF00845310
()Doi:10.1016/S0022-328X(00)83008-9
(1981)Doi:10.1021/ja01864a601
(1940)Doi:10.1016/S0040-4039(00)71463-8
(1980)Doi:10.1002/ardp.19813141009
(1981)Doi:10.1016/j.tetlet.2007.07.196
(2007)