A. Zamri et Ma. Abdallah, An improved stereocontrolled synthesis of pyochelin, siderophore of Pseudomonas aeruginosa and Burkholderia cepacia, TETRAHEDRON, 56(2), 2000, pp. 249-256
A considerably improved stereocontrolled synthesis of pyochelin, a hydroxyp
henylthiazolinylthiazolidine type of siderophore common to most strains of
Pseudomonas aeruginosa and Burkholderia cepacia is described. 2'-(2-Hydroxy
phenyl)-2'-thiazoline-4'-carbox-aldehyde, a key molecule involved in this s
ynthesis has been prepared by reduction of 2'-(2-hydroxyphenyl)-2'-thiazoli
ne-4'-(N-methoxy,N-methyl) carboxamide with lithium aluminium hydride. The
aldehyde was further coupled with (R)-N-methylcysteine to yield pyochelin.
Under the conditions reported, epimerization at the C-4' center was conside
rably diminished. (C) 1999 Elsevier Science Ltd. All rights reserved.