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 ...
