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Anomalous enolization of 3-keto-5α-steroids

✍ Scribed by R. Gardi; P.P. Castelli; A. Ercoli

Publisher
Elsevier Science
Year
1962
Tongue
French
Weight
202 KB
Volume
3
Category
Article
ISSN
0040-4039

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✦ Synopsis

IT is generally admitted that the greater stability of A2 -over A3-5asteroidal enes determines the A2 structure of 3-keto-Z-steroid enol derivatives.ly2 This structure was actually proved for cholestanone ethyl enol ether, 3 prepared by both pyrolysis of diethylaceta14 and partial hydrogenation of cholestenone ethyl enol ether.5 Now we found that 3-keto-5a-steroid enol ethers with anomalous A3structure can be easily obtained by carrying out catalytical hydrogenation of A4-3-ketone enol ethers in the presence of small amounts of an inorganic or organic base. Thus for instance, testosterone 17-acetate 3-ethyl enol ether [m.p. 130-132 o,6 [a], -145' (Di)] hydrogenated in tetrahydrofuranmethanol containing pyridine or sodium hydroxide in the presence of Pd over A1203 yielded 3-ethoxy-A3-5o-androstene-17p-ol acetate (II), m.p. ill-114', [a], t5' (Di).7 Hydrogenation carried out in the same conditions, but in

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