title: Highly efficient borylation Suzuki coupling process for 4-bromo-2-ketothiazoles: straightforward access to micrococcinate and saramycetate esters.
abstract: The first palladium-catalyzed borylation of 4-bromo-2-ketothiazoles followed by a Suzuki cross-coupling reaction with haloheteroaromatics using Buchwald's Cy-JohnPhos and XPhos ligands is reported. The methodology has allowed the fast preparation of highly valuable 4-pyridinyl- and 4-thiazolyl-2-ketothiazoles as common subunits of thiopeptide antibiotics. As direct applications, novel concise syntheses of a sulfomycinamate thio-analogue as well as micrococcinate and saramycetate esters are described.
authors.affiliation: UMR 6014 COBRA, CNRS, INSA de Rouen et Universite de Rouen, Institut de Chimie Organique Fine (IRCOF) INSA de Rouen, BP08, 76131 Mont Saint Aignan, France.
authors.forename: Thibaut
authors.initials: T
authors.lastname: Martin
authors.forename: Claire
authors.initials: C
authors.lastname: Laguerre
authors.forename: Christophe
authors.initials: C
authors.lastname: Hoarau
authors.forename: Francis
authors.initials: F
authors.lastname: Marsais
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004952:Esters; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D004952:Esters; D013844:Thiazoles; D010165:Palladium