Radical oxidation of 17-functionalized 14alpha-hydroxy steroids

V.A. Khripach; V.N. Zhabinskii; A.I. Kotyatkina; G.P. Fando; Y.Y. Zhiburtovich; A.S. Lyakhov; A.A. Govorova; M.B. Groen; J. van der Louw; A. de Groot

doi:10.1135/cccc20011764

Radical oxidation of 17-functionalized 14alpha-hydroxy steroids

V.A. Khripach, V.N. Zhabinskii, A.I. Kotyatkina, G.P. Fando, Y.Y. Zhiburtovich, A.S. Lyakhov, A.A. Govorova, M.B. Groen, J. van der Louw, A. de Groot

Organic Chemistry

Research output: Contribution to journal › Article › Academic › peer-review

13 Citations (Scopus)

Abstract

The radical oxidation of 14a-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 14a-hydroxy-17-oxo steroid (lead tetraacetate version of the hypoiodite reaction) proceeded smoothly with formation of the 13,14-secosteroid in up to 85"ield. The structure and conformation of the formed 13a-iodo-3a,5-cyclo-13,14-seco-5a-androst-5-ene-14,17-dione was determined by X-ray analysis

Original language	English
Pages (from-to)	1764-1776
Journal	Collection of Czechoslovak Chemical Communications
Volume	66
DOIs	https://doi.org/10.1135/cccc20011764
Publication status	Published - 2001

Keywords

Ceric ammonium nitrate
Conformation analysis
Fragmentation
Lead tetraacetate
Radical oxidations
Secosteroids
Steroids

Access to Document

10.1135/cccc20011764

Cite this

@article{3417815031b04c8cac30ee9f81be71c1,

title = "Radical oxidation of 17-functionalized 14alpha-hydroxy steroids",

abstract = "The radical oxidation of 14a-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 14a-hydroxy-17-oxo steroid (lead tetraacetate version of the hypoiodite reaction) proceeded smoothly with formation of the 13,14-secosteroid in up to 85{"}ield. The structure and conformation of the formed 13a-iodo-3a,5-cyclo-13,14-seco-5a-androst-5-ene-14,17-dione was determined by X-ray analysis",

keywords = "Ceric ammonium nitrate, Conformation analysis, Fragmentation, Lead tetraacetate, Radical oxidations, Secosteroids, Steroids",

author = "V.A. Khripach and V.N. Zhabinskii and A.I. Kotyatkina and G.P. Fando and Y.Y. Zhiburtovich and A.S. Lyakhov and A.A. Govorova and M.B. Groen and \{van der Louw\}, J. and \{de Groot\}, A.",

year = "2001",

doi = "10.1135/cccc20011764",

language = "English",

volume = "66",

pages = "1764--1776",

journal = "Collection of Czechoslovak Chemical Communications",

issn = "0010-0765",

publisher = "Czech Academy of Sciences",

}

TY - JOUR

T1 - Radical oxidation of 17-functionalized 14alpha-hydroxy steroids

AU - Khripach, V.A.

AU - Zhabinskii, V.N.

AU - Kotyatkina, A.I.

AU - Fando, G.P.

AU - Zhiburtovich, Y.Y.

AU - Lyakhov, A.S.

AU - Govorova, A.A.

AU - Groen, M.B.

AU - van der Louw, J.

AU - de Groot, A.

PY - 2001

Y1 - 2001

N2 - The radical oxidation of 14a-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 14a-hydroxy-17-oxo steroid (lead tetraacetate version of the hypoiodite reaction) proceeded smoothly with formation of the 13,14-secosteroid in up to 85"ield. The structure and conformation of the formed 13a-iodo-3a,5-cyclo-13,14-seco-5a-androst-5-ene-14,17-dione was determined by X-ray analysis

AB - The radical oxidation of 14a-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 14a-hydroxy-17-oxo steroid (lead tetraacetate version of the hypoiodite reaction) proceeded smoothly with formation of the 13,14-secosteroid in up to 85"ield. The structure and conformation of the formed 13a-iodo-3a,5-cyclo-13,14-seco-5a-androst-5-ene-14,17-dione was determined by X-ray analysis

KW - Ceric ammonium nitrate

KW - Conformation analysis

KW - Fragmentation

KW - Lead tetraacetate

KW - Radical oxidations

KW - Secosteroids

KW - Steroids

U2 - 10.1135/cccc20011764

DO - 10.1135/cccc20011764

M3 - Article

SN - 0010-0765

VL - 66

SP - 1764

EP - 1776

JO - Collection of Czechoslovak Chemical Communications

JF - Collection of Czechoslovak Chemical Communications

ER -

Radical oxidation of 17-functionalized 14alpha-hydroxy steroids

Abstract

Keywords

Access to Document

Fingerprint

Cite this