The Journal of Organic Chemistry

Synthesis of the chromophore of pseudobactin, a fluorescent siderophore from Pseudomonas

T Kolasa, MJ Miller

Index: Kolasa, Teodozyj; Miller, Marvin J. Journal of Organic Chemistry, 1990 , vol. 55, # 14 p. 4246 - 4255

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Citation Number: 32

Abstract

Protected forms of dihydroxyphenylalanine (DOPA) were converted to the corresponding dihydroquinolin-2-ones 13 by nitration and reductive cyclization. Subsequent N-alkylation with 0-halo-7-aminobutryic 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 ...