Synthesis of the Chromophore of Pseudobactin, a Fluorescent Siderophore from Pseudomonas

Article abstract of DOI:10.1021/jo00301a008

Protected forms of dihydroxyphenylalanine (DOPA) were converted to the corresponding dihydroquinolin-2-ones 13 by nitration and reductive cyclization.Subsequent N-alkylation with α-halo-γ-aminobutyric acid derivatives provided the carbon framework 12 for the chromophore of pseudobactin.Conversion to protected forms of the fluorescent chromophore 5 was accomplished by reaction of 12 with Lawesson's reagent to produce the corresponding thioamide which was cyclized by reaction with mercuric acetate.