A novel siderophore analog (
4) has been designed to facilitate iron transport-mediated drug delivery and drug release. This mixed ligand siderophore analog includes three bidentate ligands intended to octahedrally coordinate iron (III). The ligands include a 2,3-dihydroxy benzoic acid moiety,
N5-acetyl-
N5-hydroxy-
l-ornithine, and a β-
N-hydroxy-
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,β-diaminopropionic acid derivative. The total synthesis of
15, a form of
4 that is suitably protected, yet contains a free carboxylic acid for subsequent drug conjugation, is described.