Abstract

REYES MORENO, Mayra et al. Oxidation Reactions in 9α-Halosteroids by Jones Reagent. J. Mex. Chem. Soc [online]. 2007, vol.51, n.4, pp.232-236. ISSN 1870-249X.

Current investigations guided to searching androstane derivatives with potential anabolic activity, weakly androgenic one directed us to synthesize 3β,11β-dihydroxy-9α-halo-5α-androstane-17-ones (4a-c). These compounds were oxidized by Jones' Reagent at 0^oC obtaining a selective oxidation of the equatorial 3β-hydroxyl group. This behaviour could be explained by the high steric hindrance at the 11 β-position, increased by the strong inductive effect of the halogen atom at C-9α over the electronic density of the H-11α.

Keywords : Oxidation; androstane; anabolic activity; stereochemistry.

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