Oxidation Reactions in 9α-Halosteroids by Jones Reagent
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 0ºC 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.
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| Main Authors: | , , , , , , , , |
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| Format: | Digital revista |
| Language: | English |
| Published: |
Sociedad Química de México A.C.
2007
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| Online Access: | http://www.scielo.org.mx/scielo.php?script=sci_arttext&pid=S1870-249X2007000400012 |
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