The synthesis of 13α-androsta-5,16-diene derivatives with carboxylic acid, ester and carboxamido functionalities at position-17 via palladium-catalyzed carbonylation

Péter Ács, Attila Takács, Antal Szilágyi, J. Wölfling, G. Schneider, L. Kollár

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

17-Alkoxycarbonyl- and 17-carboxamido-3β-hydroxy-13α-androsta-5,16-diene derivatives were synthetized in high yields in the palladium-catalyzed carbonylation reactions of the corresponding 3β-hydroxy-17-iodo-13α-androsta-5,16-diene. This substrate with a 17-iodo-16-ene functionality was obtained from the 17-keto derivative via its 17-hydrazone, which was treated with iodine in the presence of a base (1,1,3,3-tetramethylguanidine). 17-Carboxamides were obtained by chemoselective aminocarbonylation through the use of amines, including amino acid esters, as N-nucleophiles. The 17-methoxycarbonyl-16-ene derivative was synthetized by using methanol as O-nucleophile. The parent compound of this series, the 17-carboxylic acid derivative, was formed in the presence of water via hydroxycarbonylation.

Original languageEnglish
Pages (from-to)419-423
Number of pages5
JournalSteroids
Volume74
Issue number4-5
DOIs
Publication statusPublished - Apr 2009

Fingerprint

Carbonylation
Hydrazones
Palladium
Carboxylic Acids
Iodine
Amines
Methanol
Esters
Derivatives
Amino Acids
Nucleophiles
Water
compound 17
1,1,3,3-tetramethylguanidine
Substrates

Keywords

  • 13α-steroid
  • Carbonylation
  • Carboxamide
  • Iodoalkene
  • Palladium
  • Steroid

ASJC Scopus subject areas

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

Cite this

The synthesis of 13α-androsta-5,16-diene derivatives with carboxylic acid, ester and carboxamido functionalities at position-17 via palladium-catalyzed carbonylation. / Ács, Péter; Takács, Attila; Szilágyi, Antal; Wölfling, J.; Schneider, G.; Kollár, L.

In: Steroids, Vol. 74, No. 4-5, 04.2009, p. 419-423.

Research output: Contribution to journalArticle

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