A concise total synthesis of (-)-indolactam v

Toshiharu Noji, Kentaro Okano, Hidetoshi Tokuyama

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

One-pot synthesis of tryptophanol derivative from N-Boc-aziridine and indole has been developed. The ring opening reaction of the aziridine takes place smoothly at -30°C in a regioselective manner and tolerates a wide range of functional groups including halogens attached to the aromatic ring, which was also performed on a gram scale. The resulting tryptophanol derivative was converted to (-)-indolactam V from commercially available 4-bromoindole through a copper-mediated aryl amination in nine steps with an overall yield of 32%.

Original languageEnglish
Pages (from-to)3833-3837
Number of pages5
JournalTetrahedron
Volume71
Issue number23
DOIs
Publication statusPublished - 2015 May 26

Keywords

  • Amino acid
  • Aziridine
  • Indolactam
  • Indole
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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