- Bioconversion of 17β-hydroxy-17α-methyl-androsta-1,4-dien-3-one and androsta-1,4-diene-3,17-dione in cultures of the green alga T76 Scenedesmus quadricauda
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Exogenous 17β-hydroxy-17α-methyl-androsta-1,4-dien-3-one and androsta-1,4-diene-3,17-dione are biotransformed by the green alga T76 Scenedesmus quadricauda. The bioproducts have been isolated by chromatographic processes and identified on the basis of their spectroscopic features. Hydration of the Δ4 double bond may justify the presence of the epimeric 5-hydroxyderivatives while rather complex skeleton rearrangements are involved in the formation of the remaining products.
- DellaGreca, Marina,Previtera, Lucio,Fiorentino, Antonio,Pinto, Gabriele,Pollio, Antonino
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- A (2)H N.M.R. study of the Steroidal Dienone-Phenol Rearrangement
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The extent of deuteriation is reported for the products of the dienone-phenol rearrangement of androsta-1,4-dien-3-ones using as catalysts (i) deuteriated acetic anhydride, acetic acid, and zinc chloride; (ii) deuterium bromide; and (iii) methanol, ethyl orthoformate, and sulphuric acid.The stereochemistry of the acid-catalysed enolization of 1-dehydrotestosterone is also reported.
- Avent, Antony G.,Hanson, James R.,Yang-zhi, Ling,Sadler, Ian H.
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p. 2129 - 2132
(2007/10/02)
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- The Preparation and Dienone-Phenol Rearrangement of Androsta-2,5-diene-4,17-dione
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The preparation of androsta-2,5-diene-4,17-dione from dehydroisoandrosterone is described.Its dienone-phenol rearrangement, in the presence of hydrobromic acid and glacial acetic acid, affords 1-methyl-4-hydroxy-estra-1,3,5(10)-trien-17-one.
- Hanson, James R.,Raines, David,Knights, Steve G.
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p. 1311 - 1313
(2007/10/02)
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