The multicomponent approach to N-methyl peptides: Total synthesis of antibacterial (-)-viridic acid and analogues
Two syntheses of natural viridic acid, an unusual triply N-methylated peptide with two anthranilate units, are presented. The first one is based on peptide-coupling strategies and affords the optically active natural product in 20% overall yield over six steps. A more economical approach with only four steps leads to the similarly active racemate by utilizing a Ugi four-component reaction (Ugi-4CR) as the key transformation. A small library of viridic acid analogues is readily available to provide first SAR insight. The biological activities of the natural product and its derivatives against the Gram-negative bacterium Aliivibrio fischeri were evaluated.
Neves Filho, Ricardo A. W.,Stark, Sebastian,Westermann, Bernhard,Wessjohann, Ludger A.
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p. 2085 - 2090
(2013/02/22)
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