| Title: | Synthesis of the aggregation pheromone of the Colorado potato beetle from its degradation product |
| Author(s): | Waclawczyk-Biedron W; Frackowiak-Wojtasek B; Strub D; Rzechak M; Wojtasek H; |
| Address: | "Faculty of Chemistry, Opole University, Ul. Oleska 48, 45-052 Opole, Poland. Department of Bioorganic Chemistry, Faculty of Chemistry, Wroclaw University of Technology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland. Faculty of Chemistry, Opole University, Ul. Oleska 48, 45-052 Opole, Poland. Electronic address: Hubert.Wojtasek@uni.opole.pl" |
| DOI: | 10.1016/j.bmcl.2015.06.083 |
| ISSN/ISBN: | 1464-3405 (Electronic) 0960-894X (Linking) |
| 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" |
| Keywords: | Animals Coleoptera/*metabolism Colorado Ketones/*chemical synthesis/chemistry/*metabolism Pheromones/*chemical synthesis/chemistry/*metabolism Solanum tuberosum/parasitology Stereoisomerism Aggregation pheromone Butanediacetals Colorado potato beetle Pher; |
| Notes: | "MedlineWaclawczyk-Biedron, Weronika Frackowiak-Wojtasek, Bozena Strub, Daniel Rzechak, Magdalena Wojtasek, Hubert eng Research Support, Non-U.S. Gov't England 2015/07/15 Bioorg Med Chem Lett. 2015 Sep 1; 25(17):3560-3. doi: 10.1016/j.bmcl.2015.06.083. Epub 2015 Jun 30" |
