118446-23-4

Upstream product

• 119437-72-8 Methyl 2-(2-hydroxyphenyl)-2-thiazoline-4-carboxylate 
• 118491-87-5 2-(4-(hydroxymethyl)-4,5-dihydrothiazol-2-yl)phenol 
• 611-20-1 salicylonitrile 
• 338461-20-4 (4S)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid N-methoxy-N-methylamide 

Downstream Products

• 69772-54-9 Neopyochelin I 
• 69772-54-9 Pyochelin II 
• 69772-54-9 (4'S,2''R,4''R)-2'-(2-hydroxyphenyl)-3''-methyl-2'',3'',4'',4',5'-hexahydro-[2,4']-bisthiazolyl-4''-carboxylic acid 
• 69772-54-9 (4'R,2''R,4''R)-2'-(2-hydroxyphenyl)-3''-methyl-2'',3'',4'',4',5'-hexahydro-[2,4']-bisthiazolyl-4''-carboxylic acid 
• 118491-87-5 2-(4-(hydroxymethyl)-4,5-dihydrothiazol-2-yl)phenol 

Relevant academic research and scientific papers

Convergent Total Synthesis of the Siderophore Piscibactin as Its Ga3+Complex

The siderophore piscibactin is a key virulence factor involved in the iron uptake of pathogenic bacteria Photobacterium damselae subsp. piscicida and Vibrio anguillarum, responsible for the fish diseases photobacterioisis (pasteurellosis) and vibriosis, respectively. A convergent total synthesis of its Ga3+ complex using l-/d-cysteine as chiral agents and Meldrum's acid is described. A Staudinger reduction/Aza-Wittig process in the synthesis of the acid-sensitive β-hydroxy-2,4-disubstituted thiazoline moiety and the convenient protecting groups was a key step in this synthesis.

Stereochemical assignment of the pyochelins

The synthesis of pyochelin has been much improved but gives four stereoisomers. The stereochemistry of the two naturally occurring pyochelins I and II has been assigned, based on (1) the similarity of the NMR spectra of pyochelin I methyl ester to those f