Steroidal alkenylphosphonates via palladium-catalyzed coupling reactions

Rita Skoda-Földes, László Kollár, Judit Horváth, Zoltán Tuba

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The palladium-catalyzed coupling of various 17-iodo-Δ16 steroids (17-iodo-androst-16-ene, 17-iodo-4-methyl-4-aza-androst-16-en-3-one, and 17-iodo-4-aza-androst-16-en-3-one) with dialkyl phosphites (dimethyl phosphite, diethyl phosphite, and diisopropyl phosphite) was examined in detail. The only successful condition for homogeneous coupling involved carrying out the reaction in the absence of any solvents. A large excess of dialkyl phosphite was used, which means that the phosphite itself acted as a solvent. Eight new androst-16-ene derivatives with phosphonate groups at C-17 were synthesized and characterized. These steroids are of pharmacological interest as potential 5α-reductase inhibitors. Under the same conditions, methylation of lactam NH was observed using dimethyl phosphite.

Original languageEnglish
Pages (from-to)791-795
Number of pages5
JournalSteroids
Volume60
Issue number12
DOIs
Publication statusPublished - Dec 1995

Keywords

  • coupling reaction of steroids
  • homogeneous palladium(0) catalysts
  • steroidal alkenylphosphonates

ASJC Scopus subject areas

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

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