Highly efficient borylation Suzuki coupling process for 4-bromo-2-ketothiazoles: straightforward access to micrococcinate and saramycetate esters

Thibaut Martin; Claire Laguerre; Christophe Hoarau; Francis Marsais

doi:10.1021/ol901525t

Highly efficient borylation Suzuki coupling process for 4-bromo-2-ketothiazoles: straightforward access to micrococcinate and saramycetate esters

Org Lett. 2009 Aug 20;11(16):3690-3. doi: 10.1021/ol901525t.

Authors

Thibaut Martin¹, Claire Laguerre, Christophe Hoarau, Francis Marsais

Affiliation

¹ 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.

PMID: 19624105
DOI: 10.1021/ol901525t

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Catalysis
Esters
Molecular Structure
Palladium / chemistry*
Thiazoles / chemical synthesis*
Thiazoles / chemistry

Substances

Anti-Bacterial Agents
Esters
Thiazoles
Palladium