Synthesis of novel steroid alkaloids by cyclization of arylimines from estrone

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Abstract

Intramolecular Lewis or Bransted acid-catalyzed cyclization reactions of steroid arylimines 6 yielded either tetrahydroquinolines condensed to the estrane skeleton 9 or N-arylamino-D-homosteroids 12-16, depending on the substituent of the arylimino group.

Original languageEnglish
Pages (from-to)3013-3020
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number11
DOIs
Publication statusPublished - Nov 1999

Keywords

  • Cycloadditions
  • Domino reactions
  • Iminium ions
  • Lewis acids
  • Quinolines

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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