Synthesis of Triarylpyridines in Thiopeptide Antibiotics by Using a C-H Arylation/Ring-Transformation Strategy

Kazuma Amaike, Kenichiro Itami, Junichiro Yamaguchi

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

We have described a C-H arylation/ring-transformation strategy for the synthesis of triarylpyridines, which form the core structure of thiopeptide antibiotics. This synthetic method readily gave 2,3,6-triarylpyridines in a regioselective manner by a two-phase approach: C-H arylation (a nickel-catalyzed decarbonylative Suzuki-Miyaura cross-coupling and decarbonylative C-H coupling for the synthesis of 2,4-diaryloxazoles) and ring transformation ([4+2] cycloaddition of 2,4-diaryloxazoles with (hetero)arylacrylic acids). To showcase these methods, we have accomplished the formal synthesis of thiopeptide antibiotics GE2270 s and amythiamicins.

Original languageEnglish
Pages (from-to)4384-4388
Number of pages5
JournalChemistry (Weinheim an der Bergstrasse, Germany)
Volume22
Issue number13
DOIs
Publication statusPublished - 2016 Mar 18
Externally publishedYes

Keywords

  • C−H arylation
  • decarbonylative coupling
  • nickel catalysis
  • ring transformation
  • total synthesis

ASJC Scopus subject areas

  • Medicine(all)

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