Highly efficient borylation Suzuki coupling process for 4-bromo-2-ketothiazoles: straightforward access to micrococcinate and saramycetate esters.
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.
Martin
Thibaut
T
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.
Laguerre
Claire
C
Hoarau
Christophe
C
Marsais
Francis
F
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
D000900:Anti-Bacterial Agents; D004952:Esters; D013844:Thiazoles; D010165:Palladium