Hydrogenation of a Tetrasubstituted Double Bond: Synthesis of 5-Methyl-19-nor-5β-pregnanes

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Title:Hydrogenation of a Tetrasubstituted Double Bond: Synthesis of 5-Methyl-19-nor-5β-pregnanes
Creators:
Kasal, Alexander
Polman, Jiří
Buděšínský, Miloš
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 10, pp. 1549-1563
Uncontrolled Keywords:<sup>1</sup>H NMR spectroscopy, Partial hydrolysis, Configuration, Hydrogenolysis, Steroids, Partial acetylation, Westphalen rearrangement, Partial oxidation

Abstract

Reduction of C=C and/or C=O bonds in 5-methyl-19-nor-5β-pregn-9-ene-3,20-dione (<strong>1</strong>) leads to saturated and unsaturated ketones and hydroxy ketones. The C=C reduction affords mainly 9β,10β and 9α,10β dihydro products. Reaction conditions of partial esterification, hydrolysis and oxidation were elaborated. Several analogues were prepared for the testing of gestagenic and neurosteroidal activities.

Title:Hydrogenation of a Tetrasubstituted Double Bond: Synthesis of 5-Methyl-19-nor-5β-pregnanes
Creators:
Kasal, Alexander
Polman, Jiří
Buděšínský, Miloš
Uncontrolled Keywords:<sup>1</sup>H NMR spectroscopy, Partial hydrolysis, Configuration, Hydrogenolysis, Steroids, Partial acetylation, Westphalen rearrangement, Partial oxidation
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. 1549-1563
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19981549UNSPECIFIED
ID Code:1401
Item Type:Article
Deposited On:06 Feb 2009 17:09
Last Modified:06 Feb 2009 16:09

Citation

Kasal, Alexander; Polman, Jiří; Buděšínský, Miloš (1998) Hydrogenation of a Tetrasubstituted Double Bond: Synthesis of 5-Methyl-19-nor-5β-pregnanes. Collection of Czechoslovak Chemical Communications, 63 (10). pp. 1549-1563. ISSN 0010-0765

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