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

29 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

Fingerprint

Antibiotics
Anti-Bacterial Agents
Cycloaddition Reaction
Nickel
Cycloaddition
Acids
GE 2270 A

Keywords

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

ASJC Scopus subject areas

  • Medicine(all)

Cite this

Synthesis of Triarylpyridines in Thiopeptide Antibiotics by Using a C-H Arylation/Ring-Transformation Strategy. / Amaike, Kazuma; Itami, Kenichiro; Yamaguchi, Junichiro.

In: Chemistry (Weinheim an der Bergstrasse, Germany), Vol. 22, No. 13, 18.03.2016, p. 4384-4388.

Research output: Contribution to journalArticle

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