249749-40-4Relevant academic research and scientific papers
Total synthesis of thiangazole
Akaji, Kenichi,Kiso, Yoshiaki
, p. 10685 - 10694 (2007/10/03)
A method for total synthesis of thiangazole (1), a tris-thiazoline- oxazole metabolite, is described. The key intermediate 9, a linear tetrapeptide amide composed of three S-benzyl-2-methylcysteine residues and a O-benzyl-threonine amide, was synthesized in 4 steps using 2-chloro-1,3- dimethyl-imidazolidium hexafluorophosphate(CIP)mediated activation. The successive thiazoline/oxazole rings were constructed by TiCl4mediated cycledehydration followed by acid-catalyzed Robinson-Gabriel reaction without difficulty.
