Facile synthesis of 12-carboxamido-11-spirostenes via palladium-catalyzed carbonylation reactions

Péter Ács, Erno Müller, Gábor Czira, Sándor Mahó, Mariette Perreira, László Kollár

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20 Citations (Scopus)

Abstract

12-Carboxamido- and 12-carboxyl-11-spirostenes were synthesized from the corresponding 12-iodo-11-ene derivative in palladium-catalyzed carbonylation reactions under mild reaction conditions. The synthesis of the iodo-alkene substrate is based on the transformation of the 12-keto derivative (hecogenin) to hydrazone, which was treated with iodine in the presence of a base (1,1,3,3-tetramethyl guanidine). While various 12-carboxamides were synthesized in moderate to high yields by using simple alkyl/arylamines or amino acid methylesters as N-nucleophiles, low yields can be achieved with alcohols as O-nucleophiles. The homogeneous carbonylation reactions tolerate the 3-hydroxy substituent and the spiroacetal moiety.

Original languageEnglish
Pages (from-to)875-879
Number of pages5
JournalSteroids
Volume71
Issue number10
DOIs
Publication statusPublished - Oct 1 2006

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Keywords

  • Carbonylation
  • Carboxamide
  • Hecogenin
  • Iodo-alkenene
  • Palladium-catalyst

ASJC Scopus subject areas

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

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