Anions of dilhaoacetic derivaives : key reagents in phosphoenolpyruvate lyases and synthase inhibitor antibiotics design
Les anions des dérivés d'acides dihalogénoacétiques : des réactifs clés pour la conception d'antibiotiques inhibiteurs de phosphoénolpyruvate lyases et de la chitine-synthétase
Abstract
Darzens reaction between dialdosugars and anions derived from alkyl dihaloacetates affords C-glycosyl glycidic esters and [alpha]-ketoesters, which are key compounds in biologically active molecules synthesis. New antibiotics are needed because of increase of the bacteria resistance towards actual drugs. This target leads to phosphoenolpyruvate lyases inhibitors for their ability to prevent Gram-negativ bacteria cellular wall growth. The glycosylated phosphoenol pyruvates are obtained by Perkow reaction trialkylphosphite and [alpha]-haloglycidic esters of [beta]-halo[alpha]-keteosters. Derivatives of [alpha]-bromocarboxylicacids are produced by reaction between dibromoacetonitrile and dialdosugars and then easily transformed into C-glycosyl [alpha]aminoacids. These compounds represent valuable chirons to afford a large panel of biologically active products. This new methodology is used here to synthesize Polyoxins, excellent agricultural fungicides.
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