10147-53-2Relevant academic research and scientific papers
Formation of 5α steroids by biotranformation involving the 5 α-reductase activity of Penicillium decumbens
Holland, Herbert L.,Dore, Sophia,Xu, Weili,Brown, Frances M.
, p. 642 - 647 (1994)
The biotransformation of a series of Δ4-3-ketosteroids by the Penicillium decumbens ATCC 10436 has been investigated. Conversion to the 5α-dihydrosteroid was observed substrates of the androsterone and pregne series: the reaction is tolerant of non-polar substituents (Cl and CH3) at C-4 of the substrate, but does not occur in the presence of a 4-hydroxyl group, or with additional unsaturation at the Δ1 or Δ6 positions. A-nor, B-nor, 3-deoxy-, and 3,5-cycloandrostanes are not reduced, but 6-methylenestestosterone is converted to a 6-methylene-5α-dihydro derivative. Several biotransformations are reported which involve oxidoreductase activity at C-3 and/or C-17, either concomitant or independent of Δ4 reduction: the substrate specificity of the oxidoreductase processes has been examined and defined by the use of 3α-hydroxy, 3β-hydroxy, 3-keto, 17β-keto substituted steroids. In this way, the existence in P. decumbens of 3β-hydroxy-3-keto and 17β-hydroxy-17-keto oxidoreductases has been demonstrated.
Regioselectivity of the Reaction of 3-Keto Steroids with Potassium Superoxide
Alvarez, Enrique,Francisco, Cosme G.,Freire, Raimundo,Hernandez, Rosendo,Salazar, Jose A.,et al.
, p. 1523 - 1526 (2007/10/02)
The regioselectivity in the oxidation of different types of 3-keto steroids with potassium superoxide in the presence of 18-crown-6 has been investigated.In all cases, the reaction products are directly related to the enolization process of the substrates.The oxidation of a 2-enolate results in oxidative cleavage of ring A with loss of carbon monoxide to give the lactols (2) and (10) and aldehyde (8).However, the oxidation of 4-enolates occurs with oxidative cleavage of ring A to give the ketones (7) and (12), the latter with loss of carbon monoxide.
