Synthesis of 5,10-seco analogs of testosterone

V.A. Khripach; V.N. Zhabinskii; A.I. Kuchto; Y.Y. Zhiburtovich; N.B. Khripach; A.S. Lyakhov; M.B. Groen; J. van der Louw; Æ. de Groot

doi:10.1016/j.steroids.2008.07.005

Synthesis of 5,10-seco analogs of testosterone

V.A. Khripach, V.N. Zhabinskii, A.I. Kuchto, Y.Y. Zhiburtovich, N.B. Khripach, A.S. Lyakhov, M.B. Groen, J. van der Louw, Æ. de Groot

Organic Chemistry

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

1 Citation (Scopus)

Abstract

A number of 5,10-seco analogs of testosterone has been synthesized starting from products of the radical oxidation of 3 beta,17 beta-diacetoxy-5 alpha-androstan-5 alpha-ol. The obtained compounds possess a flexible 10-membered ring with substituents (=O, -OH) at C-3 and C-5. Similar derivatives with an (E)- and (Z)-Delta(1(10))-double bond have been prepared also. X-ray analysis and a combination of NMR experiments have been used for their structure elucidation and conformation analysis. (C) 2008 Published by Elsevier Inc.

Original language	English
Pages (from-to)	1424-1432
Journal	Steroids
Volume	73
Issue number	14
DOIs	https://doi.org/10.1016/j.steroids.2008.07.005
Publication status	Published - 2008

Keywords

medium-sized ring
radical oxidation
10-membered ring
steroids
conformations
secosteroids
reactivity

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10.1016/j.steroids.2008.07.005

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title = "Synthesis of 5,10-seco analogs of testosterone",

abstract = "A number of 5,10-seco analogs of testosterone has been synthesized starting from products of the radical oxidation of 3 beta,17 beta-diacetoxy-5 alpha-androstan-5 alpha-ol. The obtained compounds possess a flexible 10-membered ring with substituents (=O, -OH) at C-3 and C-5. Similar derivatives with an (E)- and (Z)-Delta(1(10))-double bond have been prepared also. X-ray analysis and a combination of NMR experiments have been used for their structure elucidation and conformation analysis. (C) 2008 Published by Elsevier Inc.",

keywords = "medium-sized ring, radical oxidation, 10-membered ring, steroids, conformations, secosteroids, reactivity",

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

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T1 - Synthesis of 5,10-seco analogs of testosterone

AU - Khripach, V.A.

AU - Zhabinskii, V.N.

AU - Kuchto, A.I.

AU - Zhiburtovich, Y.Y.

AU - Khripach, N.B.

AU - Lyakhov, A.S.

AU - Groen, M.B.

AU - van der Louw, J.

AU - de Groot, Æ.

N1 - ISI:000261751600010

PY - 2008

Y1 - 2008

N2 - A number of 5,10-seco analogs of testosterone has been synthesized starting from products of the radical oxidation of 3 beta,17 beta-diacetoxy-5 alpha-androstan-5 alpha-ol. The obtained compounds possess a flexible 10-membered ring with substituents (=O, -OH) at C-3 and C-5. Similar derivatives with an (E)- and (Z)-Delta(1(10))-double bond have been prepared also. X-ray analysis and a combination of NMR experiments have been used for their structure elucidation and conformation analysis. (C) 2008 Published by Elsevier Inc.

AB - A number of 5,10-seco analogs of testosterone has been synthesized starting from products of the radical oxidation of 3 beta,17 beta-diacetoxy-5 alpha-androstan-5 alpha-ol. The obtained compounds possess a flexible 10-membered ring with substituents (=O, -OH) at C-3 and C-5. Similar derivatives with an (E)- and (Z)-Delta(1(10))-double bond have been prepared also. X-ray analysis and a combination of NMR experiments have been used for their structure elucidation and conformation analysis. (C) 2008 Published by Elsevier Inc.

KW - medium-sized ring

KW - radical oxidation

KW - 10-membered ring

KW - steroids

KW - conformations

KW - secosteroids

KW - reactivity

U2 - 10.1016/j.steroids.2008.07.005

DO - 10.1016/j.steroids.2008.07.005

M3 - Article

VL - 73

SP - 1424

EP - 1432

JO - Steroids

JF - Steroids

SN - 0039-128X

IS - 14

ER -