title: Synthesis of the aggregation pheromone of the Colorado potato beetle from its degradation product.
abstract: 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.
authors.affiliation: Faculty of Chemistry, Opole University, Ul. Oleska 48, 45-052 Opole, Poland.
authors.forename: Weronika
authors.initials: W
authors.lastname: Wacławczyk-Biedroń
authors.affiliation: Faculty of Chemistry, Opole University, Ul. Oleska 48, 45-052 Opole, Poland.
authors.forename: Bożena
authors.initials: B
authors.lastname: Frąckowiak-Wojtasek
authors.affiliation: Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland.
authors.forename: Daniel
authors.initials: D
authors.lastname: Strub
authors.affiliation: Faculty of Chemistry, Opole University, Ul. Oleska 48, 45-052 Opole, Poland.
authors.forename: Magdalena
authors.initials: M
authors.lastname: Rzechak
authors.affiliation: Faculty of Chemistry, Opole University, Ul. Oleska 48, 45-052 Opole, Poland. Electronic address: Hubert.Wojtasek@uni.opole.pl.
authors.forename: Hubert
authors.initials: H
authors.lastname: Wojtasek
mesh_terms: D000818:Animals; D001517:Coleoptera / Q000378:metabolism*; D003120:Colorado; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D010675:Pheromones / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D011198:Solanum tuberosum / Q000469:parasitology; D013237:Stereoisomerism
chemical_list: C000607567:(S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one; D007659:Ketones; D010675:Pheromones; C029750:methylheptenone
keywords: Aggregation pheromone; Butanediacetals; Colorado potato beetle; Pheromone inactivation