Lengthening of the Alkyl Chain in Steroid O-(ω-Carboxyalkyl)oximes by Wittig Reaction

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Title:Lengthening of the Alkyl Chain in Steroid O-(ω-Carboxyalkyl)oximes by Wittig Reaction
Creators:
Pouzar, Vladimír
Slavíková, Tereza
Černý, Ivan
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 10, pp. 1623-1634
Uncontrolled Keywords:Wittig reaction, Steroids, Swern oxidation, Horner-Emmons reaction, <i>O</i>-Alkyloximes

Abstract

The steroid <i>O</i>-alkyloximes with various alkyl length (2-4 carbons) and with terminal hydroxyl groups were oxidized to aldehydes and their Wittig reaction with triethyl phosphonoacetate was studied. Oximes derived from 17-oxoandrost-5-en-3β-yl acetate and from 7-oxo and 19-oxocholest-5-en-3β-yl acetate were used. Except of 7- and 19-[<i>O</i>-(2-hydroxyethyl)]oximes, all the hydroxyalkyloximes gave successively aldehydes and corresponding unsaturated esters. The method is useful for the lengthening of the carbon chain in ω-substituted <i>O</i>-alkyloximes.

Title:Lengthening of the Alkyl Chain in Steroid O-(ω-Carboxyalkyl)oximes by Wittig Reaction
Creators:
Pouzar, Vladimír
Slavíková, Tereza
Černý, Ivan
Uncontrolled Keywords:Wittig reaction, Steroids, Swern oxidation, Horner-Emmons reaction, <i>O</i>-Alkyloximes
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. 1623-1634
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19981623UNSPECIFIED
ID Code:1407
Item Type:Article
Deposited On:06 Feb 2009 17:09
Last Modified:06 Feb 2009 16:09

Citation

Pouzar, Vladimír; Slavíková, Tereza; Černý, Ivan (1998) Lengthening of the Alkyl Chain in Steroid O-(ω-Carboxyalkyl)oximes by Wittig Reaction. Collection of Czechoslovak Chemical Communications, 63 (10). pp. 1623-1634. ISSN 0010-0765

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