| Title: | Alternative synthesis of the Colorado potato beetle pheromone |
| Author(s): | Faraldos JA; Coates RM; Giner JL; |
| Address: | "Department of Chemistry, University of Illinois , Urbana-Champaign, Illinois 61801, United States" |
| ISSN/ISBN: | 1520-6904 (Electronic) 0022-3263 (Print) 0022-3263 (Linking) |
| Abstract: | "A concise preparation of the pheromone secreted by the male Colorado potato beetle [viz. (3S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one] was accomplished in four steps starting from 2-fluoronerol or 2-fluorogeraniol. The key step in the synthesis involves a 6-endo epoxide ring-opening with ester participation that simultaneously inverts the 3R-configuration of the (3R)-2,3-epoxy-2-fluoroprenyl acetate intermediate and installs the ketone functionality of the semiochemical. Extensive NMR studies validate the proposed 6-endo mechanism of the featured rearrangement, which under anhydrous conditions resulted in the formation of two bicyclic 1,3-dioxan-5-ones via an unprecedented intramolecular Prins cyclization" |
| Keywords: | Animals Bridged Bicyclo Compounds/*chemical synthesis/chemistry Coleoptera Colorado Cyclization Dioxanes/*chemical synthesis/chemistry Magnetic Resonance Spectroscopy Male Molecular Structure Pheromones/*chemical synthesis/chemistry; |
| Notes: | "MedlineFaraldos, Juan A Coates, Robert M Giner, Jose-Luis eng R01 GM013956/GM/NIGMS NIH HHS/ GM 13956/GM/NIGMS NIH HHS/ Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S. 2013/09/21 J Org Chem. 2013 Oct 18; 78(20):10548-54. doi: 10.1021/jo4017056. Epub 2013 Oct 2" |
