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

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2001.0

Abstract

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 b-hydroxythioamide by means of Burgess reagent leading to thiazoline. Based on its synthesis, the absolute con®guration of natural yersiniabactin has been determined as 9R, 10RS, 12R, 13S and 19S. q 2001 Elsevier Science Ltd. All rights reserved.

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