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Total synthesis of exochelin MN and analogues
1Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556-5670, USA.
The Journal of Organic Chemistry
|July 6, 2002
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.