The synthesis of 17-alkoxycarbonyl- and 17-carboxamido-13α-estra-1,3,5(10),16-tetraene derivatives via palladium-catalyzed carbonylation reactions

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

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

17-Alkoxycarbonyl- and 17-carboxamido-13α-estra-1,3,5(10),16-tetraenes were synthesized from the 17-iodo-13α-estra-1,3,5(10),16-tetraene derivative in palladium-catalyzed alkoxycarbonylation and aminocarbonylation reactions, respectively. The synthesis of the 17-iodo-16-ene derivative, used as substrate, is based on the transformation of the 17-keto derivative (epiestrone methyl ether) to hydrazone, which was treated with iodine in the presence of a base (1,1,3,3-tetramethyl guanidine). 17-Carboxamides were obtained in good yields (up to 88%) not only with simple alkyl/aryl amines but also with amino acid methyl esters as N-nucleophiles. The use of alcohols as O-nucleophiles in alkoxycarbonylation resulted in the corresponding 17-esters; however, yields of synthetic interest were obtained only with methanol.

Original languageEnglish
Pages (from-to)669-675
Number of pages7
JournalSteroids
Volume73
Issue number6
DOIs
Publication statusPublished - Jul 2008

Fingerprint

Carbonylation
Palladium
Nucleophiles
Esters
Derivatives
Methyl Ethers
Hydrazones
Guanidine
Iodine
Amines
Methanol
Alcohols
Amino Acids
Substrates

Keywords

  • 13α-Steroid
  • Carbonylation
  • Carboxamide
  • Iodo-alkene
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology
  • Molecular Biology

Cite this

The synthesis of 17-alkoxycarbonyl- and 17-carboxamido-13α-estra-1,3,5(10),16-tetraene derivatives via palladium-catalyzed carbonylation reactions. / Ács, Péter; Takács, Attila; Szilágyi, Antal; Wölfling, J.; Schneider, G.; Kollár, L.

In: Steroids, Vol. 73, No. 6, 07.2008, p. 669-675.

Research output: Contribution to journalArticle

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