6533b857fe1ef96bd12b500f
RESEARCH PRODUCT
Synthesis of the aggregation pheromone of the Colorado potato beetle from its degradation product
Bożena Frąckowiak-wojtasekHubert WojtasekDaniel StrubWeronika Wacławczyk-biedrońMagdalena Rzechaksubject
ColoradoKetoneClinical BiochemistryPharmaceutical ScienceBiochemistryPheromoneschemistry.chemical_compoundbutanediacetalsDrug DiscoveryColorado potato beetleAnimalsOrganic chemistryMolecular BiologyGlycolic acidSolanum tuberosumchemistry.chemical_classificationbiologyChemistrySilica gelOrganic ChemistryColorado potato beetleSubstrate (chemistry)StereoisomerismKetonesbiology.organism_classificationColeopteraBiochemistrySex pheromoneMolecular MedicinePheromoneStereoselectivitypheromone inactivationaggregation pheromonedescription
Incubation of the Colorado potato beetle aggregation pheromone, (S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one, with antennal or leg extracts from this beetle gave 6-methyl-5-hepten-2-one as the major product. This ketone was used as a substrate in a stereoselective synthesis of the pheromone. It was attached to the butanediacetal of glycolic acid with good stereoselectivity and the desired isomer was further enriched by purification of the product of this reaction on silica gel.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2015-09-01 | Bioorganic & Medicinal Chemistry Letters |