Synthetic studies of thiazoline and thiazolidine-coataining natural products. Part 3:Total synthesis and absolute configuration of the siderophore yersiniabactin

摘要

Total synthesis of yersiniabactin, a siderophore from cultures of the bacterium Yersinia enterocolitica, was accomplished. Chirality at the readily recemizable C-9 carbon was preserved during cyclization of #beta#-hydroxythioamide by means of Burgess reagent leading to thiazoline. Based on its synthesis, the absolute configuration of natural yersiniabactin has been determined as 9R, 10RS, 12R, 13S and 19S.