The formation of 3α- and 3β-methoxy-Δ4-androsten-17-one and Δ3,5-androstadien-17-one by acid-catalyzed methanolysis
1963; Elsevier BV; Volume: 1; Issue: 6 Linguagem: Inglês
10.1016/s0039-128x(63)80094-x
ISSN1878-5867
Autores Tópico(s)Cancer Treatment and Pharmacology
Resumo— 3α- and 3β-Methoxy-Δ4-androsten-17-one (IVb and Vb) were produced along with a smaller amount of Δ3,5-androstadien-17-one when the 17-ethylene ketal (I) of Δ4-androstene-3,17-dione was reduced with sodium borohydride and the resulting mixture of epimeric 3-alcohols was refluxed in methanol containing acetic acid and water. The predominance of the exchange reaction with methanol over elimination is explicable on the basis of steric hindrance from C-19. Proof of structure for the previously unreported epimeric methoxy compounds was obtained by a study of their chemical and physical properties. The epimer with an equatorial methoxyl group proved to be faster moving in an adsorption system of chromatography in contrast to expectation based on the known rate of movement of epimeric 3-hydroxy compounds.
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