Stereoselective synthesis of androstane-based steroidal phosphine oxides possessing the 16α-diphenylphosphinyl moiety

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Abstract

New steroidal phosphine oxides were obtained by base-catalysed addition of HPPh2 to the C=C double bond of α,β-unsaturated steroidal esters. The presence of Pd(OAc)2 has been shown to accelerate the reaction rate. 16 α-Phosphinyl-17β-metoxycarbonyl-androstane derivatives were formed stereoselectively and isolated in moderate to high yields. The exact structure of the products were determined by various spectroscopic methods including two-dimensional NMR techniques.

Original languageEnglish
Pages (from-to)2825-2832
Number of pages8
JournalSynthetic Communications
Volume36
Issue number19
DOIs
Publication statusPublished - Sep 1 2006

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Keywords

  • H-P addition
  • Palladium
  • Phosphine oxide
  • Steroids

ASJC Scopus subject areas

  • Organic Chemistry

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