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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

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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.

Graphical abstract: 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

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Publication details

The article was received on 21 Nov 2017, accepted on 08 Dec 2017 and first published on 02 Jan 2018


Article type: Communication
DOI: 10.1039/C7OB02866K
Citation: Org. Biomol. Chem., 2018, Advance Article
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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

    P. Lassalas, C. Berini, J. E. Y. Rouchet, J. Hédouin, F. Marsais, C. Schneider, C. Baudequin and C. Hoarau, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB02866K

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