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Note | Regular issue | Vol 57, No. 5, 2002, pp.903-908
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9458
A Synthesis of a Hydroxyvaline-derived Thiazole-4-carboxylate Constituting an Antibiotic, Thiocilline I

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

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


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 NaBH4, followed by oxidation with Dess-Martin reagent gave the corresponding formyl derivative, which was then thiazolated with H-L-Cys-OMe to give 2.