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

Total synthesis of yersiniabactin, a siderophore from cultures of the bacterium Yersinia enterocolitica, was accomplished. Chirality at the readily racemizable 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. (C) 2001 Elsevier Science Ltd. All rights reserved.