Miyaura borylation/Suzuki–Miyaura coupling (MBSC) sequence of 4-bromo-2,4′-bithiazoles with halides: straightforward access to a heterocylic cluster of D-series of thiopeptide GE2270

Pierrik Lassalas (1) , Christophe Berini (1) , Jean-Baptiste Rouchet (1) , Jonathan Hédouin (1) , Francis Marsais (1) , Cédric Schneider (1) , Christine Baudequin (1) , Christophe Hoarau (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

Herein, palladium-catalyzed Miyaura borylation of 4-bromo-2,4′-bithiazoles followed by Suzuki–Miyaura cross-coupling reaction (named the MBSC process) with (hetero)aryl- and alkenyl halides is reported. This methodology offers rapid access to various 2′,4-disubstituted 2,4′-bithiazole features including naturally-occurring 4-alkenylated and 4-pyridinylated 2,4′-bithiazoles. To prove its application, a concise approach for the synthesis of a heterocyclic cluster of the thiopeptide D-series antibiotic GE2270 is reported through a late-stage MBSC strategy.

Domaines: Chimie

Pierrik Lassalas, Christophe Berini, Jean-Baptiste Rouchet, Jonathan Hédouin, Francis Marsais, et al.. Miyaura borylation/Suzuki–Miyaura coupling (MBSC) sequence of 4-bromo-2,4′-bithiazoles with halides: straightforward access to a heterocylic cluster of D-series of thiopeptide GE2270. Organic & Biomolecular Chemistry, 2018, 16 (4), pp.526-530. ⟨10.1039/c7ob02866k⟩. ⟨hal-02024509⟩