Synthesis of 13,14-secotestosterone derivatives.

Abstract:

:A number of testosterone analogs with a 13,14-secosteroidal fragment have been prepared from (13S)-13-iodo-6beta-methoxy-3alpha, 5-cyclo-13,14-seco-5alpha-androstan-14,17-dione. The key steps involved stereoselective deiodination of the starting compound with triphenylphosphine and selective protection of the 17-keto group with trimethylsilylcyanide. Removal of iodine at C-13 proceeded with inversion of the configuration at C-13, which has been established by X-ray crystallography. 13,14-Secotestosterone analogues substituted and non-substituted at C-14 have been prepared. The obtained compounds containing flexible CD ring fragments are of great interest for comparative studies in biological tests together with testosterone and other steroids with a rigid tetracyclic skeleton.

journal_name

Steroids

journal_title

Steroids

authors

Khripach VA,Zhabinskii VN,Kuchto AI,Zhiburtovich YY,Fando GP,Lyakhov AS,Govorova AA,Groen MB,van der Louw J,de Groot A

doi

10.1016/j.steroids.2004.04.010

subject

Has Abstract

pub_date

2004-07-01 00:00:00

pages

501-9

issue

7

eissn

0039-128X

issn

1878-5867

pii

S0039128X04000686

journal_volume

69

pub_type

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