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-ket...

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Published inOrganic letters Vol. 11; no. 16; pp. 3690 - 3693
Main Authors Martin, Thibaut, Laguerre, Claire, Hoarau, Christophe, Marsais, Francis
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.08.2009
Amer Chemical Soc
Subjects
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Catalysis
Chemistry
Chemistry, Organic
Esters
Molecular Structure
Palladium - chemistry
Physical Sciences
Science & Technology
Thiazoles - chemical synthesis
Thiazoles - chemistry
HETEROCYCLIC CORE
HALIDES
PALLADIUM-CATALYZED BORYLATION
OXAZOLE
CONCISE TOTAL-SYNTHESIS
GE2270-A
BIARYL SYNTHESIS
THIAZOLE
THIOPEPTIDE ANTIBIOTICS
ARYL CHLORIDES
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol901525t