Total Synthesis of Exochelin MN and Analogues
The Journal of Organic Chemistry2002Vol. 67(14), pp. 4759–4770
Citations Over TimeTop 10% of 2002 papers
Abstract
The first total synthesis of exochelin MN is described along with rationally designed analogues. The required L-threo-beta-hydroxyamino acid components were constructed using either Sharpless asymmetric aminohydroxylation reactions or an aldol reaction of imidazolidinone 19. A new concise procedure for the preparation of the constituent six-membered cyclic hydroxamate was developed. In addition, a plausible mechanism for exochelin MN-mediated iron(III) transport was proposed. Biological studies of these compounds will be used to evaluate this hypothesis.
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