Epalons: Synthesis of 3α,7α-Dihydroxy-5α-pregnan-20-one

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Title:Epalons: Synthesis of 3α,7α-Dihydroxy-5α-pregnan-20-one
Creators:
Chodounská, Hana
Kasal, Alexander
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 10, pp. 1543-1548
Uncontrolled Keywords:7α-Hydroxylase, Steroids, Solvolysis, GABA<sub>A</sub>-Modulator, L-Selectride®, 3α,5α-Tetrahydroprogesterone, Epalon

Abstract

3α,7α-Dihydroxy-5α-pregnan-20-one (<strong>12</strong>) was prepared from (20<i>R</i>)-pregn-5-ene-3β,20-diyl 3-acetate 20-benzoate (<strong>1</strong>). ∆<sup>5</sup>-Olefin was oxidized in an allylic position and hydrogenated. Inversion of a configuration at carbon C-3 was carried out by solvolysis in <i>N</i>,<i>N</i>-dimethylformamide of 3β-tosylate in the presence of sodium nitrite. For stereoselective reduction of the 7-oxo group, L-Selectride&reg; was used.

Title:Epalons: Synthesis of 3α,7α-Dihydroxy-5α-pregnan-20-one
Creators:
Chodounská, Hana
Kasal, Alexander
Uncontrolled Keywords:7α-Hydroxylase, Steroids, Solvolysis, GABA<sub>A</sub>-Modulator, L-Selectride®, 3α,5α-Tetrahydroprogesterone, Epalon
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:63
Number:10
Page Range:pp. 1543-1548
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19981543UNSPECIFIED
ID Code:1400
Item Type:Article
Deposited On:06 Feb 2009 17:09
Last Modified:06 Feb 2009 16:09

Citation

Chodounská, Hana; Kasal, Alexander (1998) Epalons: Synthesis of 3α,7α-Dihydroxy-5α-pregnan-20-one. Collection of Czechoslovak Chemical Communications, 63 (10). pp. 1543-1548. ISSN 0010-0765

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