Radical Oxidation of 17-Functionalized 14α-Hydroxy Steroids

[img]PDF - Authorized users only
Language: English
152Kb
Title:Radical Oxidation of 17-Functionalized 14α-Hydroxy Steroids
Creators:
Khripach, Vladimir A.
Zhabinskii, Vladimir N.
Kotyatkina, Anna I.
Fando, Galina P.
Zhiburtovich, Yuliya Y.
Lyakhov, Alexander S.
Govorova, Alla A.
Groen, Marinus B.
Louw, Jaap van der
Groot, Aede de
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 66, 12, pp. 1764-1776
Uncontrolled Keywords:Radical oxidations, Ceric ammonium nitrate, Conformation analysis, Secosteroids, Steroids, Lead tetraacetate, Fragmentation

Abstract

The radical oxidation of 14α-hydroxy steroids with various functional groups at C-17 was studied. Lead tetraacetate and ceric ammonium nitrate were used as oxidizing agents. It was shown that reactions of this type afforded complex mixtures of compounds. However, the radical oxidation of 14α-hydroxy-17-oxo steroid (lead tetraacetate version of the hypoiodite reaction) proceeded smoothly with formation of the 13,14-secosteroid in up to 85% yield. The structure and conformation of the formed 13α-iodo-3α,5-cyclo-13,14-seco-5α-androst-5-ene-14,17-dione was determined by X-ray analysis. <p>

Title:Radical Oxidation of 17-Functionalized 14α-Hydroxy Steroids
Creators:
Khripach, Vladimir A.
Zhabinskii, Vladimir N.
Kotyatkina, Anna I.
Fando, Galina P.
Zhiburtovich, Yuliya Y.
Lyakhov, Alexander S.
Govorova, Alla A.
Groen, Marinus B.
Louw, Jaap van der
Groot, Aede de
Uncontrolled Keywords:Radical oxidations, Ceric ammonium nitrate, Conformation analysis, Secosteroids, Steroids, Lead tetraacetate, Fragmentation
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:66
Number:12
Page Range:pp. 1764-1776
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20011764UNSPECIFIED
ID Code:1894
Item Type:Article
Deposited On:06 Feb 2009 17:13
Last Modified:06 Feb 2009 16:13

Citation

Khripach, Vladimir A.; Zhabinskii, Vladimir N.; Kotyatkina, Anna I.; Fando, Galina P.; Zhiburtovich, Yuliya Y.; Lyakhov, Alexander S.; Govorova, Alla A.; Groen, Marinus B.; Louw, Jaap van der; Groot, Aede de (2001) Radical Oxidation of 17-Functionalized 14α-Hydroxy Steroids. Collection of Czechoslovak Chemical Communications, 66 (12). pp. 1764-1776. ISSN 0010-0765

Repository Staff Only: item control page