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  • 1
    Electronic Resource
    Electronic Resource
    Synthesis and oxidation of pregna-3,5-dien-20-ols and -20-one and selective reduction of pregna-3,5-dien-20-one (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 213-215 
    Details
    ISSN: 0170-2041
    Keywords: Steroids ; Pregna-3,5-dien-20-one, oxidation, reduction ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Pregna-3,5-dien-20-one (4) and (20S)- and (20R)-pregna-3,5-dien-20-ol (2 and 3) were synthesized from progesterone. Oxidation of a mixture of 2 and 3 with Jones reagent gave 4, while a large excess of Jones reagent afforded besides 4, 6-oxoprogesterone (5), 6β-hydroxyprogesterone (6) and 5α-pregnane-3,6,20-trione (7). With L-selectride as reducing agent, reduction of 4 led to 2 and 3 in a ratio of about 1:1. However, some reducing agents gave a higher ratio of isomer 3.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199019900139
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  • 2
    Electronic Resource
    Electronic Resource
    Borane Reduction of the Steroid 20-Ketone Group in the Presence of Various Chiral β-Amino Alcohols (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 581-582 
    Details
    ISSN: 0170-2041
    Keywords: 5β-Pregnane, 3α-hydroxy-20-one ; Chiral borane reduction ; Borane reduction ; Steroids ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The direction of reduction of 20-carbonyl group of 3α-hydroxy-5β-pregnan-20-one (1) with a complex of borane-methyl sulfide and chiral β-amino alcohols, depends on the chirality of the amino alcohol. Where there is a 2-phenyl or 2-benzyl substituent, then the S enantiomer gives exclusively the steroid 20R alcohol 3. The R enantiomer of 2-amino-2-phenyl-1-ethanol gives the highest steroid 20S (2):20R (3) alcohol ratio.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199319930194
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    Paper (German National Licenses)
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