Synthesis of (19E)-3,20-dioxopregn-4-en-19-al 19-(O-carboxymethyl)oxime

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Title:Synthesis of (19E)-3,20-dioxopregn-4-en-19-al 19-(O-carboxymethyl)oxime
Creators:
Fajkoš, Jan
Pouzar, Vladimír
Vereš, Karel
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 5, pp. 1087-1092

Abstract

Hydride reduction of the ketone <i>I</i> gave the (20<i>R</i>)-hydroxy derivative <i>II</i>. Cleavage of the diacetate <i>III</i> with zinc dust, followed by mild Jones’ oxidation led to the aldehyde <i>V</i>. Oximation with (O-carboxymethyl)hydroxylamine hemihydrochloride and methylation with diazomethane afforded the ester <i>VI</i>. Alkaline hydrolysis to the acid catalyzed rearrangement afforded the dione <i>IX</i>. Mild hydrolysis gave the desired hapten <i>X</i> derived from progesterone.

Title:Synthesis of (19E)-3,20-dioxopregn-4-en-19-al 19-(O-carboxymethyl)oxime
Creators:
Fajkoš, Jan
Pouzar, Vladimír
Vereš, Karel
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:56
Number:5
Page Range:pp. 1087-1092
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19911087UNSPECIFIED
ID Code:5026
Item Type:Article
Deposited On:22 Feb 2010 11:28
Last Modified:22 Feb 2010 10:29

Citation

Fajkoš, Jan; Pouzar, Vladimír; Vereš, Karel (1991) Synthesis of (19E)-3,20-dioxopregn-4-en-19-al 19-(O-carboxymethyl)oxime. Collection of Czechoslovak Chemical Communications, 56 (5). pp. 1087-1092. ISSN 0010-0765

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