Synthesis of the heterocyclic core of the D-series GE2270

Christophe Berini (1) , Thibaut Martin (1) , Pierrik Lassalas (1) , Francis Marsais (1) , Christine Baudequin (1) , Christophe Hoarau (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

A straightforward enantiomerically pure synthesis of the heterocyclic core of the D-series GE2270 is reported. The synthetic strategy combines the Hantzsch thiazole’s building condensation with a cross-coupling reaction including direct C–H hetarylation to build and connect step-by-step thiazolyl moieties to the 5-bromopicolinate as readily available starting material.

Keywords: Bromination; Antibiotic; Hantzsch synthesis; Cross-coupling; BSC; Thiopeptide; C–H arylation

Domains: Chemical Sciences

Christophe Berini, Thibaut Martin, Pierrik Lassalas, Francis Marsais, Christine Baudequin, et al.. Synthesis of the heterocyclic core of the D-series GE2270. Beilstein Journal of Organic Chemistry, 2017, 13, pp.1407-1412. ⟨10.3762/bjoc.13.137⟩. ⟨hal-02046259⟩