6533b861fe1ef96bd12c4d2d
RESEARCH PRODUCT
Total Synthesis of (+)-Phenguignardic Acid, a Phytotoxic Metabolite ofGuignardia bidwellii
Alexander StoyeTill OpatzDanuta Kowalczyksubject
Natural productbiologyStereochemistryMetaboliteOrganic ChemistryAbsolute configurationTotal synthesisGuignardiaFungusbiology.organism_classificationchemistry.chemical_compoundchemistryOrganic chemistryCarboxylatePhysical and Theoretical ChemistryEnantiomerdescription
(+)-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 |
|---|---|---|---|---|
| 2013-07-24 | European Journal of Organic Chemistry |