The oxidation of progesterone under GoAggIII conditions

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Title:The oxidation of progesterone under GoAggIII conditions
Creators:
Barton, Derek H. R.
Doller, Dario
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 5, pp. 984-990

Abstract

The oxidation of pregn-4-ene-3,20-dione (progesterone) by the GoAgg<sup>III</sup> system (aqueous hydrogen peroxide, ferric chloride, picolinic acid in pyridine-acetic acid solution) has been investigated. Two tri-keto derivatives were isolated and identified as pregn-4-ene-3,6,20-trione and pregn-4-ene-3,12,20-trione. The third major product isolated was identified as the unstable 5α-formyl-A-nor-pregnane-3,20-dione, which deformylated spontaneously to A-nor-5β-pregnane-3,20-dione. A mechanism for the A-ring contraction is proposed, based upon the participation of a carbon-Fe(V) intermediate.

Title:The oxidation of progesterone under GoAggIII conditions
Creators:
Barton, Derek H. R.
Doller, Dario
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. 984-990
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19910984UNSPECIFIED
ID Code:5016
Item Type:Article
Deposited On:22 Feb 2010 11:28
Last Modified:22 Feb 2010 10:28

Citation

Barton, Derek H. R.; Doller, Dario (1991) The oxidation of progesterone under GoAggIII conditions. Collection of Czechoslovak Chemical Communications, 56 (5). pp. 984-990. ISSN 0010-0765

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