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

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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 languageEnglish
Pages (from-to)1424-1432
JournalSteroids
Volume73
Issue number14
DOIs
Publication statusPublished - 2008

Keywords

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

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