A synthesis of a hydroxyvaline-derived thiazole-4-carboxylate constituting an antibiotic, thiocilline I

摘要

A convenient synthesis of an important constituent segment, methyl (2S)-2-[1-(N-Boc)amino-2-hydroxy-2-methyl]propylthiazole-4-carboxylate (2), which is the Fragment C derivative of a macrocyclic antibiotic, thiocilline, is described. Reduction of methyl N-Boc-hydroxyvalinate (4) with NaBH_4, followed by oxidation with Dess-Martin reagent gave the coresponding formyl derivative, which was then thiazolated with H-L-Gys-OMe to give 2.