Heck reactions of steroidal alkenyl iodides

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

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Heck reactions of some steroid derivatives possessing iodo-alkenyl moiety (17-iodo-androst-16-ene, 1, 17-iodo-4-aza-4-methyl-androst-16-en-3- one, 2, 17-iodo-4-aza-androst-16-en-3-one, 3) were carried out in the presence of palladium catalysts using various olefins (methyl acrylate, ethyl methacrylate, allyl alcohol and allyl acetate) as coupling partners. With methyl acrylate, a side reaction was observed: the coupling product underwent a Diels-Alder reaction with the excess of methyl acrylate resulting in a six- membered carbocyclic E-ring. Reaction conditions of the synthesis of the Heck-product were optimized. Although the coupling with allyl alcohol led to the formation of 21-formyl-16-pregnene derivatives, the synthesis of the corresponding steroidal unsaturated alcohol could be achieved only via hydrolysis of the coupling product of the alkenyl iodide with allyl acetate.

Original languageEnglish
Pages (from-to)93-98
Number of pages6
JournalSteroids
Volume63
Issue number2
DOIs
Publication statusPublished - Feb 1 1998

    Fingerprint

Keywords

  • 17-iodo-androst-16-ene derivatives
  • Dienes
  • Homogeneous coupling reaction
  • Palladium catalysts

ASJC Scopus subject areas

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

Cite this