Synthesis of new thiazole analogues of pyochelin, a siderophore of Pseudomonas aeruginosa and Burkholderia cepacia.: A new conversion of thiazolines into thiazoles

Three pyochelin analogues and their methyl esters all containing a thiazole ring have been synthesised from the same Weinreb amide key intermediate. One of these analogues called HPTT-COOH, a molecule released in the course of pyochelin and yersiniabactin biosynthesis, was efficiently synthesised using a new base induced conversion of the key compound 2'-(2-hydroxyphenyl)-2'-thiazoline-4'-(N-methoxy,N-methyl) carboxamide into 2'-(2-hydroxyphenyl)-2'-thiazole-4'-(N-methoxy,N-methyl) carboxamide. (C) 2004 Elsevier Ltd. All rights reserved.