Concise Total Syntheses of Pyrido[4,3-b]carbazole Alkaloids Using Copper-Mediated 6π-Electrocyclization

Tomoki Itoh, Takumi Abe, Tominari Choshi, Takashi Nishiyama, Reiko Yanada, Minoru Ishikura

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

Abstract

Concise syntheses of 9-methoxyellipticine, 3,4-dihydroellipticine (μ-alkaloid D), 1,2,3,4-tetrahydroellipticine, 2-methyl-1,2,3,4-tetrahydroellipticine, olivacine, 3,4-dihydroolivacine, (±)-guatambuine, and (±)-janetine were developed starting from hexatriene intermediates readily obtained by Pd-catalyzed tandem cyclization/cross-coupling reaction of indolylborates. The route enables the facile construction of pyrido[4,3-b]carbazoles by Cu-catalyzed 6π-electrocyclization and subsequent transformation of the pyridocarbazole intermediates into pyrido[4,3-b]carbazole alkaloids. Concise total syntheses of pyrido[4,3-b]carbazole alkaloids were accomplished using Cu-catalyzed 6π-electrocyclization of hexatriene as a key step.

Original languageEnglish
Pages (from-to)2290-2299
Number of pages10
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number13
DOIs
Publication statusPublished - May 1 2016
Externally publishedYes

Keywords

  • Alkaloids
  • Copper
  • Electrocyclization
  • Natural products
  • Nitrogen heterocycles
  • Total synthesis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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