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Synthesis of the Heterocyclic Core of the GE 2270 Antibiotics and Structure Elucidation of a Major Degradation Product
Author(s) -
Heckmann Golo,
Bach Thorsten
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200461715
Subject(s) - diastereomer , pyridine , degradation (telecommunications) , sequence (biology) , product (mathematics) , stereochemistry , chemistry , combinatorial chemistry , organic chemistry , computer science , biochemistry , mathematics , telecommunications , geometry
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.