Concise Total Syntheses of Paullone and Kenpaullone via Cyanide-Catalyzed Intramolecular Imino-Stetter Reaction

Sang Eun Lee, Seong Jong Lee, Cheol-Hong Cheon

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

Highly concise total syntheses of paullone and kenpaullone were developed. Cyanide-catalyzed intramolecular imino-Stetter reaction of aldimines derived from methyl 2-aminocinnamate derivatives and 2-nitrobenzaldehyde provided 2-(2′-nitrophenyl)indole-3-acetic acid derivatives. Subsequent reduction of the nitro group with zinc under acidic conditions to an amino group followed by spontaneous lactam formation allowed for the total syntheses of paullone and kenpaullone to be completed in two steps starting from commercially available materials. The direct use of a nitro group as the precursor of an amino group present in the phenyl ring at the 2-position in the indole ring significantly streamlined the total syntheses of these target molecules.

Original languageEnglish
JournalSynthesis (Germany)
DOIs
Publication statusAccepted/In press - 2017 Feb 22

Keywords

  • cyanide-catalyzed imino-Stetter reaction
  • kenpaullone
  • paullone
  • total synthesis
  • umpolung of aldimines

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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