Synthesis of Substituted Quinolizidines via a Gold-Catalyzed Double Cyclization Cascade

Shiori Nonaka, Kenji Sugimoto, Hirofumi Ueda, Hidetoshi Tokuyama

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

A novel synthesis of quinolizidines by a cationic gold-catalyzed double cyclization cascade has been developed. The reaction was initiated by the gold-catalyzed 6-exo-dig cyclization of ynamides, which was followed by a second cyclization of an enamide intermediate to provide the corresponding quinolizidine derivatives. The utility of this reaction was demonstrated by application to the synthesis of multi-substituted quinolizidines and by the total synthesis of a quinolizidine alkaloid, (±)-lupinine.

Original languageEnglish
Pages (from-to)380-385
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume358
Issue number3
DOIs
Publication statusPublished - 2016 Feb 4

Keywords

  • alkaloids
  • cyclization
  • domino reaction
  • gold
  • quinolizidines

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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