A novel one-pot synthesis of carbazole-1,4-quinones through Pd-catalyzed cyclocarbonylation, desilylation and oxidation processes from 3-iodo-2-propenylindoles

Mami Fujii, Takashi Nishiyama, Tominari Choshi, Nanase Satsuki, Takaya Fujiwaki, Takumi Abe, Minoru Ishikura, Satoshi Hibino

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11 Citations (Scopus)

Abstract

A novel one-pot synthesis of carbazole-1,4-quinone by consecutive Pd-catalyzed cyclocarbonylation, desilylation, and oxidation reactions is described. We propose a possible mechanism of the cyclocarbonylation reaction between 3-iodo-2-propenylindole and CO (1 atm) in the presence of a tributyl(vinyl)tin and Pd-catalyst and the resulting acylpalladium species was directly coupled with a terminal alkene to produce the carbazole-1,4-quinone. To our knowledge, this is the first example of this type of reaction. A new formal total synthesis of a carbazole-1,4-quinone alkaloid, murrayaquinone A was established using this reaction.

Original languageEnglish
Pages (from-to)1805-1810
Number of pages6
JournalTetrahedron
Volume70
Issue number9
DOIs
Publication statusPublished - Mar 4 2014
Externally publishedYes

Keywords

  • Carbazole-1,4-quinone
  • Cyclocarbonylation
  • Murrayaquinone A
  • One-pot synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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