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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
Abstract : 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.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02024509
Contributor : Madeleine Roux-Merlin Connect in order to contact the contributor
Submitted on : Tuesday, February 19, 2019 - 11:09:58 AM
Last modification on : Tuesday, January 4, 2022 - 4:04:59 AM

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CNRS | INSA-ROUEN | COMUE-NORMANDIE | UNIROUEN | COBRA | INC-CNRS | INSA-GROUPE | ENSICAEN | UNILEHAVRE | UNICAEN

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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 and Biomolecular Chemistry, Royal Society of Chemistry, 2018, 16 (4), pp.526-530. ⟨10.1039/c7ob02866k⟩. ⟨hal-02024509⟩

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