Palladium-catalyzed cross-coupling reaction of indolylborates and its application for the syntheses of indole alkaloids

Takumi Abe, Minora Ishikura

Research output: Contribution to journalReview articlepeer-review

2 Citations (Scopus)

Abstract

In our continuing study of the reactivity and synthetic application of indolylborate as a versatile synthetic intermediate, we found that the use of indolylborate in palladium-catalyzed cross -coupling reaction is highly effective for the synthesis of indole derivatives. The present account deals with the results concerning a novel approach to indole alkaloids based on the use of the palladium-catalyzed cross-coupling. Dimeric indole alkaloid, yuechuke, was synthesized through the palladium-catalyzed carbonylative cross-coupling reaction. Pyridocarbazole alkaloids (ellip-ticine, olivacine, and their related alkaloids), and indolophenanthridine alkaloid (calothrixins A and B) were obtained by the use of cyclization/cross-coupling domino reaction. In addition, (CuOTf) 2 toluene complex was demonstrated to catalyze 6π-electrocyclization of hexatrienes, leading to pyrido [4,3-b] carbazoles.

Original languageEnglish
Pages (from-to)117-129
Number of pages13
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume74
Issue number2
DOIs
Publication statusPublished - 2016
Externally publishedYes

Keywords

  • Carbonylative cross - Coupling reaction
  • Copper-catalyzed 6π-electrocyclization
  • Cyclization/cross-coupling domino reaction
  • Indole alkaloids
  • Indolylborate

ASJC Scopus subject areas

  • Organic Chemistry

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