β-selective C-H arylation of pyrroles leading to concise syntheses of lamellarins C and I

Kirika Ueda, Kazuma Amaike, Richard M. Maceiczyk, Kenichiro Itami, Junichiro Yamaguchi

Research output: Contribution to journalArticlepeer-review

83 Citations (Scopus)

Abstract

The first general β-selective C-H arylation of pyrroles has been developed by using a rhodium catalyst. This C-H arylation reaction, which is retrosynthetically straightforward but results in unusual regioselectivity, could result in de novo syntheses of pyrrole-derived natural products and pharmaceuticals. As such, we have successfully synthesized polycyclic marine pyrrole alkaloids, lamellarins C and I, by using this β-selective arylation of pyrroles with aryl iodides (C-H/C-I coupling) and a new double C-H/C-H coupling as key steps.

Original languageEnglish
Pages (from-to)13226-13232
Number of pages7
JournalJournal of the American Chemical Society
Volume136
Issue number38
DOIs
Publication statusPublished - 2014 Sep 24
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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