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Communication | Special issue | Vol 61, No. 1, 2003, pp.45-50
Published online, 4th August, 2003
DOI: 10.3987/COM-03-S27
Useful Synthesis of the Main Central 2,3,6-Trisubstituted Pyridine Skeleton of Various Thiostrepton-Type Macrocyclic Antibiotics

Chung-gi Shin,* Hirofumi Saito, and Yasuchika Yonezawa

*Laboratory of Organic Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan


A useful synthetic method for the main central 2-(2-oxazol-4-yl)-3- (4-thiazol-2-yl)-6-carboxypyridine skeleton [Fragment A] constructing various thiostrepton-type macrocyclic antibiotics is described, in which the precursor of Fragment A was derived from the authentic ethyl 2-(6-dimethoxymethyl-2-tri- fluoromethanesulfonyloxy-3-pyridyl)thiazole-4-carboxylate in 14 steps. Finally, the fragment condensation of Fragment A with the already prepared carboxy component dipeptide [Fragment B] proceeded first to give the precursor of Fragment A-B.