Journal of Organic Chemistry p. 4246 - 4255 (1990)
Update date:2022-08-05
Topics:
Kolasa, Teodozyj
Miller, Marvin J.
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.
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