Synthesis of the heterocyclic core of the D-series GE2270

Beilstein J Org Chem. 2017 Jul 17:13:1407-1412. doi: 10.3762/bjoc.13.137. eCollection 2017.

Abstract

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: BSC; C–H arylation; Hantzsch synthesis; antibiotic; bromination; cross-coupling; thiopeptide.