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Short Paper | Regular issue | Vol 83, No. 4, 2011, pp.867-874
Published online, 2nd March, 2011
DOI: 10.3987/COM-11-12138
Synthesis of Caboxamycin and Its Derivatives Using Eco-Friendly Oxidation

Yoshinobu Tagawa,* Hiroki Koba, Kazuhiro Tomoike, and Kunihiro Sumoto

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan


The reaction of 3-hydroxyanthranilic acid or methyl 3-hydroxyanthranilate with O-benzylsalicylaldehyde in xylenes gave benzoxazole derivatives, which lead to a novel benzoxazole antibiotic, caboxamycin via debenzylation or demethylation in good yield, in the presence of dry activated carbon and bubbling molecular oxygen. The present reaction involves the simple procedure, easy workup and environmentally benign materials such as reusable activated carbon and molecular oxygen.