Synthesis of 13,14-secotestosterone derivatives

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

Research output: Contribution to journalArticleAcademicpeer-review

9 Citations (Scopus)


A number of testosterone analogs with a 13,14-secosteroidal fragment have been prepared from (13S)-13-iodo-6-methoxy-3, 5-cyclo-13,14-seco-5-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.
Original languageEnglish
Pages (from-to)501-509
Issue number7
Publication statusPublished - 2004


  • steroids
  • stereochemistry
  • inactivation
  • secosteroids
  • inhibition
  • mechanism

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