Microbial iron chelators: total synthesis of aerobactin and its constituent amino acid, N6-acetyl-N6-hydroxylysine
PJ Maurer, MJ Miller
Index: Maurer, Peter J.; Miller, Marvin J. Journal of the American Chemical Society, 1982 , vol. 104, # 11 p. 3096 - 3101
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Citation Number: 70
Abstract
Abstract: The synthesis of the natural ferric ionophore (-)-aerobactin (1) and of its constituent amino acid N6-acetyl-N6-hydroxylysine (2) is described. The benzyl hydroxamates 8 and 9 were subjected to triphenylphosphine-diethyl azodicarboxylate-mediated alkylations with the c-hydroxynorleucine derivative 7a. While 8 gave a complex mixture with predominant carbonyl 0-alkylation, 9 was cleanly N-alkylated to yield 14. Compounds 10a, b were ...
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