Facile synthesis of 11-carboxamido-androst-4,9(11)-dienes via palladium-catalyzed aminocarbonylation

Péter Ács, Balázs Jakab, Attila Takács, László Kollár

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17 Citations (Scopus)

Abstract

11-Carboxamido-androst-4,9(11)-dienes were synthesized from the corresponding 11-iodo-androst-4,9(11)-diene derivative in palladium-catalyzed aminocarbonylation reaction under mild reaction conditions. The synthesis of the iodo-alkene substrate is based on the transformation of the 11-keto derivative to hydrazone, which was treated with iodine in the presence of a base (1,1,3,3-tetramethyl guanidine). The 11-carboxamides were synthesized in moderate to high isolated yields by using simple alkyl/arylamines or amino acid methylesters as N-nucleophiles. The highly active palladium catalysts enable the homogeneous catalytic functionalization at one of the most hindered position (C-11) of the steroidal skeleton.

Original languageEnglish
Pages (from-to)627-632
Number of pages6
JournalSteroids
Volume72
Issue number8
DOIs
Publication statusPublished - Jul 1 2007

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Keywords

  • Androstane
  • Carbonylation
  • Carboxamide
  • Iodo-alkene
  • Palladium catalyst

ASJC Scopus subject areas

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

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