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RESEARCH PRODUCT
ChemInform Abstract: Total Synthesis of (+)-Phenguignardic Acid, a Phytotoxic Metabolite of Guignardia bidwellii
Danuta KowalczykAlexander StoyeTill Opatzsubject
Natural productbiologyStereochemistryMetaboliteAbsolute configurationTotal synthesisGuignardiaGeneral MedicineFungusbiology.organism_classificationchemistry.chemical_compoundchemistryCarboxylateEnantiomerdescription
(+)-Phenguignardic acid, a phytotoxic metabolite of the grape black rot fungus Guignardia bidwellii was synthesized, as well as its enantiomer, in eight steps from (R)-phenyllactic acid and 3-phenylprop-2-yn-1-ol. The formation of the carboxylate at a late stage, to avoid enolization of the precursor used in the central acetalization step, proved to be crucial. The synthesis of the natural product allowed the unabiguous assignment of its hitherto unknown absolute configuration.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-01-31 | ChemInform |