Synthesis of ferrocene-labeled steroids via copper-catalyzed azide-alkyne cycloaddition. Reactivity difference between 2β-, 6β- and 16β-azido-androstanes

Klaudia Fehér, János Balogh, Zsolt Csók, Tamás Kégl, László Kollár, Rita Skoda-Földes

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12 Citations (Scopus)

Abstract

Copper-catalyzed cycloaddition of steroidal azides and ferrocenyl-alkynes were found to be an efficient methodology for the synthesis of ferrocene-labeled steroids. At the same time, a great difference between the reactivity of 2β- or 16β-azido-androstanes and a sterically hindered 6β-azido steroid toward both ferrocenyl-alkynes and simple alkynes, such as phenylacetylene, 1-octyne, propargyl acetate and methyl propiolate, was observed.

Original languageEnglish
Pages (from-to)738-744
Number of pages7
JournalSteroids
Volume77
Issue number7
DOIs
Publication statusPublished - Jun 2012
Externally publishedYes

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Keywords

  • Azidosteroid
  • Copper
  • Cycloaddition
  • Ferrocene
  • Triazole

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Endocrinology
  • Molecular Biology
  • Organic Chemistry
  • Pharmacology

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