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

Research output: Contribution to journalArticle

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

Fingerprint

Androstanes
Alkynes
Azides
Cycloaddition
Cycloaddition Reaction
Copper
Steroids
ferrocene

Keywords

  • Azidosteroid
  • Copper
  • Cycloaddition
  • Ferrocene
  • Triazole

ASJC Scopus subject areas

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

Cite this

Synthesis of ferrocene-labeled steroids via copper-catalyzed azide-alkyne cycloaddition. Reactivity difference between 2β-, 6β- and 16β-azido-androstanes. / Fehér, Klaudia; Balogh, János; Csók, Zsolt; Kégl, Tamás; Kollár, László; Skoda-Földes, Rita.

In: Steroids, Vol. 77, No. 7, 06.2012, p. 738-744.

Research output: Contribution to journalArticle

Fehér, Klaudia ; Balogh, János ; Csók, Zsolt ; Kégl, Tamás ; Kollár, László ; Skoda-Földes, Rita. / Synthesis of ferrocene-labeled steroids via copper-catalyzed azide-alkyne cycloaddition. Reactivity difference between 2β-, 6β- and 16β-azido-androstanes. In: Steroids. 2012 ; Vol. 77, No. 7. pp. 738-744.
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