Reaction of (13S)-13-iodo-6beta-methoxy-3alpha,5-cyclo-13,14-seco-5alpha-androstane-14,17-dione with hydroxylamine and its application to the synthesis of new 13,14-seco steroids

V.A. Khripach, V.N. Zhabinskii, A.I. Kuchto, G.P. Fando, Y.Y. Zhiburtovich, 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)

Abstract

The synthesis of 13,14-seco steroids starting from easily available (13S)-13-iodo-6-methoxy-3,5-cyclo-13,14-seco-5-androsta-14,17-dione is described. The C-17 ketone was converted regioselectively into its oxime with simultaneous stereoselective deiodination at C-13. The remaining C-14 carbonyl group was then reduced stereoselectively with Ca(BH4)2. The configurations at the relevant stereocenters of the thus obtained hydroxy oxime were determined by X-ray analysis. Successful regeneration of the C-17 carbonyl group was achieved by treatment of the corresponding oxime acetate with TiCl3.
Original languageEnglish
Pages (from-to)511-514
JournalSteroids
Volume69
Issue number7
DOIs
Publication statusPublished - 2004

Keywords

  • medium-sized ring
  • inactivation
  • secosteroids
  • inhibition
  • mechanism
  • oxidation

Fingerprint Dive into the research topics of 'Reaction of (13S)-13-iodo-6beta-methoxy-3alpha,5-cyclo-13,14-seco-5alpha-androstane-14,17-dione with hydroxylamine and its application to the synthesis of new 13,14-seco steroids'. Together they form a unique fingerprint.

  • Cite this

    Khripach, V. A., Zhabinskii, V. N., Kuchto, A. I., Fando, G. P., Zhiburtovich, Y. Y., Lyakhov, A. S., Govorova, A. A., Groen, M. B., van der Louw, J., & de Groot, Æ. (2004). Reaction of (13S)-13-iodo-6beta-methoxy-3alpha,5-cyclo-13,14-seco-5alpha-androstane-14,17-dione with hydroxylamine and its application to the synthesis of new 13,14-seco steroids. Steroids, 69(7), 511-514. https://doi.org/10.1016/j.steroids.2004.04.006