Synthesis and oxidation of pregna‐3,5‐dien‐20‐ols and ‐20‐one and selective reduction of pregna‐3,5‐dien‐20‐one

Göndös, György; Orr, James C.

doi:10.1002/jlac.199019900139

Cited by 8 publications

(2 citation statements)

References 6 publications

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“…This was deduced by the HMBC correlations. C-20 was assigned to be R [15]. The structure of metabolite 10 was thus identified to be 15α, 20R-dihydroxy-pregna-1,4-diene-3,11-dione.…”

Section: Resultsmentioning

confidence: 99%

Biotransformation of 11-ketoprogesterone by Filamentous Fungus, <i>Fusarium lini</i>

et al. 2011

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Microbial transformation of 11-ketoprogesterone (1) by the filamentous fungi Fusarium lini was investigated. Biotransformation of 1 with F. lini resulted in the production of ten oxidative metabolites (2-11). Structures of these metabolites were deduced by spectroscopic analysis and seven of them, 5-11, were found to be new metabolites.Keywords: 11-Ketoprogesterone; Steroid; Microbial transformation; Hydroxylation; Filamentous fungi; Fusarium lini.© 2011 JSR Publications. ISSN: 2070-0237 (Print); 2070-0245 (Online). All rights reserved. doi:10.3329/jsr.v2i2.6221 J. Sci. Res. 3 (2), 347-356 (2011)

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“…This was deduced by the HMBC correlations. C-20 was assigned to be R [15]. The structure of metabolite 10 was thus identified to be 15α, 20R-dihydroxy-pregna-1,4-diene-3,11-dione.…”

Section: Resultsmentioning

confidence: 99%

Biotransformation of 11-ketoprogesterone by Filamentous Fungus, <i>Fusarium lini</i>

et al. 2011

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“…The relatively easy availability made possible its use for the diastereoselective reduction of more complicated compounds like steroids. The reduction of the keto function in position 20 to the 20α‐hydroxy isomer is relatively scarcely studied 5–7 and selectivity toward the 20α isomer was generally low. High selectivity was only achieved when organoborohydrides and electrophilic organoboranes were used 8.…”

Section: Introductionmentioning

confidence: 99%

Combined computational and experimental investigations on the diastereoselective hydrogenation of steroids by chiral oxazaborolidine

Göndös

Pálinkó

2001

Int J of Quantum Chemistry

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ABSTRACT:In this work the results of semiempirical quantum chemical calculations are described that support experimental findings applying the methyl derivative of oxazaborolidine-BH 3 chiral complex for the reduction of a number of pregnane derivatives (3α-hydroxy-5β-pregnane-20-one, 3α,17α-dihydroxy-5β-pregnane-20-one, 3α,21-dihydroxy-5β-pregnane-20-one, and 3α,17α,21-trihydroxy-5β-pregnane-20-one). Calculations were performed by the MNDO method. The reactants, the products, the assumed transition states, as well as the assumed intermediate structures were optimized without any constraints. Calculations were able to reproduce the observed activity sequence and explain the experimental finding that the thermodynamically less stable isomer is formed preferentially.

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ChemInform Abstract: Synthesis and Oxidation of Pregna‐3,5‐dien‐20‐ols and ‐20‐one and Selective Reduction of Pregna‐3,5‐dien‐20‐one.

Goendoes¹,

Orr²

1990

ChemInform

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280ChemInform Abstract NaBH4 reduction of progesterone (I) affords the (20S)-and (20R)-alcohols (II) and (III). Oxidation of this mixture with an equimolar amount of Jones reagent yields the pregna-3,5-dien-20-one (IV) as the sole isolable product, whereas a large excess of the oxidizing reagent produces a mixture of the derivatives (IV)-(VII). The selective reduction of the ketone (IV) using various reducing agents is also investigated. In general, these reactions afford mixtures of the epimeric alcohols (II) and (III), the latter being the major component. L-Selectride yields (II) and (III) in an approximately 1:1 ratio.

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Synthesis and oxidation of pregna‐3,5‐dien‐20‐ols and ‐20‐one and selective reduction of pregna‐3,5‐dien‐20‐one

Cited by 8 publications

References 6 publications

Biotransformation of 11-ketoprogesterone by Filamentous Fungus, <i>Fusarium lini</i>

Biotransformation of 11-ketoprogesterone by Filamentous Fungus, <i>Fusarium lini</i>

Combined computational and experimental investigations on the diastereoselective hydrogenation of steroids by chiral oxazaborolidine

ChemInform Abstract: Synthesis and Oxidation of Pregna‐3,5‐dien‐20‐ols and ‐20‐one and Selective Reduction of Pregna‐3,5‐dien‐20‐one.

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