Synthesis of Phaitanthrin E and Tryptanthrin through Amination/Cyclization Cascade

Takumi Abe, Masaru Terasaki

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Phaitanthrin E was biomimetically synthesized from methyl indole-3-carboxylate and methyl anthranilate or anthranilic acid using the ester group as an activating group. The reaction proceeds through NCS-mediated dearomatization/TFA-catalyzed protonation of indolenine/C(2) amination/Et3N-promoted aromatization and cyclization in one-pot procedure. This method is capable of converting simple biomass materials to phaitanthrin E. The synthesis not only allows assessment of antiproliferative activity, but also affords experimental support for the hypothetical biosynthetic pathway of phaitanthrin E. The resulting phaitanthrin E derivatives were evaluated for in vitro antiproliferative activity against human colorectal cancer cells (DLD-1). The biogenetic intermediate of phaitanthrin E showed higher antiproliferative activity than the natural product, phaitanthrin E. Furthermore, a concise synthesis of tryptanthrin is also accomplished from indole-3-carbaldehyde and methyl anthranilate using the aldehyde group as an activating group.

Original languageEnglish
Article numbere1700284
JournalHelvetica Chimica Acta
Volume101
Issue number2
DOIs
Publication statusPublished - Feb 2018
Externally publishedYes

Keywords

  • alkaloids
  • biomimetic
  • cascade reaction
  • indoles
  • synthesis

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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