Concise synthesis of pyrrolophenanthridine alkaloids using a Pd-mediated biaryl coupling reaction with regioselective C-H activation via the intramolecular coordination of the amine to Pd

Takashi Harayama, Akihiro Hori, Hitoshi Abe, Yasuo Takeuchi

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

The concise synthesis of Amaryllidaceae alkaloids, such as anhydrolycorinone, anhydrolycorin-7-one, assoanine, and oxoassoanine, which have a pyrrolophenanthridine skeleton, was achieved in moderate yield using the Pd-mediated biaryl coupling reaction of 1-(2-halobenzyl)-2,3-dihydroindole, which applied the regioselective C-H activation method with intramolecular coordination of the benzylamino group to Pd.

Original languageEnglish
Pages (from-to)1611-1616
Number of pages6
JournalTetrahedron
Volume60
Issue number7
DOIs
Publication statusPublished - Feb 9 2004

Keywords

  • Anhydrolycorine
  • Assoanine
  • Coodination
  • Palladium
  • Regioselectivity

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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