C4 Pictet-Spengler Reactions for the Synthesis of Core Structures in Hyrtiazepine Alkaloids

Takumi Abe, Tomohiro Haruyama, Koji Yamada

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

The hyrtiazepine alkaloids are a family of bisindole natural products that have the azepinoindole backbone. We developed a biomimetic approach by constructing the azepinoindole core in a one-pot manner through 1,4-diazabicyclo[2.2.2]octane/2,2,2-trifluoroethanol (DABCO/TFE) promoted Pictet-Spengler reaction onto the C-4 position of tryptophan. This strategy allowed the synthesis of common key structures of these families. The key intermediate can be converted into the 3 H -pyrano[2,3- b:5,6- e ′]diindol intermediate present in hyrtimomines A and B, as well as the azepinoindole core present in fargesine..

Original languageEnglish
Article numberss-2017-c0153-st
Pages (from-to)4141-4150
Number of pages10
JournalSynthesis (Germany)
Volume49
Issue number18
DOIs
Publication statusPublished - Sep 18 2017
Externally publishedYes

Keywords

  • azepinoindoles
  • biomimetic synthesis
  • cyclizations
  • indole alkaloids
  • Pictet-Spengler reaction
  • stereoselectivities

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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