The Multicomponent Approach to N-methyl Peptides: Total Synthesis of Antibacterial (-)-viridic Acid and Analogues

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2012 Dec 5

PMID 23209543

Citations 4

Authors

Ricardo A W Neves Filho

Sebastian Stark

Bernhard Westermann

Ludger A Wessjohann

Affiliations

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Abstract

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.

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