Total synthesis of calothrixins A and B by palladium-catalyzed tandem cyclization/cross-coupling reaction of indolylborate

Takumi Abe, Toshiaki Ikeda, Tominari Choshi, Satoshi Hibino, Noriyuki Hatae, Eiko Toyata, Reiko Yanada, Minoru Ishikura

Research output: Contribution to journalArticlepeer-review

44 Citations (Scopus)

Abstract

The palladium-catalyzed tandem cyclization/cross-coupling reaction of triethyl(indol-2-yl)borate with vinyl bromide was successfully used in the concise total synthesis of the indolophenanthridine alkaloids, calothrixins A and B. Palladium-catalyzed cross-coupling reaction of indolylborate with vinyl bromide proceeded smoothly, leading to triene. This intermediate was successfully used for the total synthesis of calothrixins A and B.

Original languageEnglish
Pages (from-to)5018-5027
Number of pages10
JournalEuropean Journal of Organic Chemistry
Issue number26
DOIs
Publication statusPublished - Sep 2012
Externally publishedYes

Keywords

  • Copper
  • Cross-coupling
  • Electrocyclic reactions
  • Palladium
  • Total synthesis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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