Synthesis of the Heterocyclic Core of the GE 2270 Antibiotics and Structure Elucidation of a Major Degradation Product

Two birds were killed with one stone by the synthesis of the trisubstituted pyridine (R,R)-1 and its diastereoisomer. In a short synthetic sequence for the construction of the GE 2270 thiazolyl peptides, 2,3,6-tribromopyridine was converted into pyridine 1 in only four steps (Bn=benzyl). In addition, the absolute and relative configuration of a major degradation product of GE 2270A was proven.