| Title: | "Concise preparation of the (3E,5Z)-alkadienyl system. New approach to the synthesis of principal insect sex pheromone constituents" |
| Author(s): | Ragoussis V; Panopoulou M; Ragoussis N; |
| Address: | "Department of Chemistry, Laboratory of Organic Chemistry, University of Athens, Panepistimiopolis Zographou, 157 71 Athens, Greece. ragousi@chem.uoa.gr" |
| ISSN/ISBN: | 0021-8561 (Print) 0021-8561 (Linking) |
| Abstract: | "A new rapid and low-cost preparation of the (3E,5Z)-3,5-alkadienyl system, encountered in several insect pheromone constituents, was developed. Knoevenagel condensation of (E)-2-alkenals with ethyl hydrogen malonate in dimethyl sulfoxide, in the presence of a catalytic amount of piperidinium acetate, led to a mixture of geometrical isomers of ethyl 3,5-alkadienoates and ethyl 2,4-alkadienoates, from which the (3E,5Z)-3,5-alkadienoate was conveniently separated, by the use of urea inclusion complex formation. The importance of this procedure has been illustrated by the preparation of the (3E,5Z)-3,5-tetradecadienoic acid (megatomoic acid) 1, the (3E,5Z)-3,5-dodecadienyl acetate 2, and the (3E,5Z)-3,5-tetradecadienyl acetate 3. These compounds are the main components of insect sex pheromones and constitute synthetic targets of considerable interest for the semiochemical community" |
| Keywords: | Alkadienes/*chemistry Animals Gas Chromatography-Mass Spectrometry Hydrogen Bonding Insecta/*chemistry Magnetic Resonance Spectroscopy Molecular Structure Sex Attractants/*chemical synthesis; |
| Notes: | "MedlineRagoussis, Valentine Panopoulou, Maria Ragoussis, Nikitas eng 2004/08/05 J Agric Food Chem. 2004 Aug 11; 52(16):5047-51. doi: 10.1021/jf049406b" |
