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 f...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2012-11, Vol.8 (1), p.2085-2090
Main Authors: Neves Filho, Ricardo A W, Stark, Sebastian, Westermann, Bernhard, Wessjohann, Ludger A
Format: Article
Language:English
Subjects:
antibiotic
anticancer
Chemistry
Full Research Paper
Gram negative bacteria
natural product
peptide coupling
peptides
peptoid
toxin
Ugi reaction
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Summary: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.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.8.234