title: Synthesis of Triarylpyridines in Thiopeptide Antibiotics by Using a C-H Arylation/Ring-Transformation Strategy.
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.
authors.affiliation: Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya, 464-8601, Japan.|Department of Chemistry, Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602, Japan.
authors.forename: Kazuma
authors.initials: K
authors.lastname: Amaike
authors.affiliation: Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya, 464-8601, Japan.|Department of Chemistry, Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602, Japan.|JST, ERATO, Itami Molecular Nanocarbon Project, Chikusa, Nagoya, 464-8602, Japan.
authors.forename: Kenichiro
authors.initials: K
authors.lastname: Itami
authors.affiliation: Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya, 464-8601, Japan. junichiro@chem.nagoya-u.ac.jp.|Department of Chemistry, Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602, Japan. junichiro@chem.nagoya-u.ac.jp.
authors.forename: Junichiro
authors.identifier: http://orcid.org/0000-0002-3896-5882
authors.initials: J
authors.lastname: Yamaguchi
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D061565:Cycloaddition Reaction; D006860:Hydrogen Bonding; D009532:Nickel / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D010455:Peptides; D010456:Peptides, Cyclic; D011725:Pyridines; D013844:Thiazoles; D009532:Nickel; C068122:GE 2270 A
keywords: C−H arylation; decarbonylative coupling; nickel catalysis; ring transformation; total synthesis