Abstract
The synthesis of the major component of the sex pheromone of the processionary mothThaumetopoea pityocampa is described. The synthesis uses the carbocupration of acetylene, followed by the coupling with the appropriate 1-iodoalkyne. This synthetic pheromone was shown to be of 98.8%Z purity.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Alexakis, A., Normant, J.F., andVillieras, J. 1976. Dérivés organocuivreux vinyliques VII. Addition de l'acétylène sur des cuprates lithiens: Synthese d'homo et d'hétℰo-vinyl-cuprates (Z).Tetrahedron Lett. 00:3461–3462.
Alexakis, A., Cahiez, G., andNormant, J. F. 1979. Vinyl-copper derivatives X: Alkylation of (Z)-dialkenyl cuprates.Synthesis 00:826–830.
Camps, F., Coll, J., Canela, R., Guerrero, A.,andRiba, M. 1981. Synthesis of the two isomers of the potential sex pheromone ofThaumetopoea pityacampa (Lepidoptera, Notodontidae) and related model compounds.Chem. Lett. 00:703–706.
Guerrero, A., Camps, F., Riba, M., Einhorn, J., Descoins, C., andLallemand, J. Y. 1981. Identification of a potential sex pheromone of the processionary mothThaumetopoea pityocampa (Lepidoptera, Notodontidae).Tetrahedron Lett. 22:2013–2016.
Lüthy, C., Konstantin, P., andUntch, K.G. 1978. Total synthesis ofdl-19-hydroxyprosta-glandin E, anddl-13-cis-15-epi-19-hydroxyprostaglandin E1.J. Am. Chem. Soc. 100:6211–6217.
Michelot, D.,Guerrero, A., andRatovelomanana, V. 1982. An efficient stereoselective synthesis of (Z)-13-hexadecen-11-ynyl acetate, a sex attractant ofThaumetopoea pityocampa (Ben. and Schiss) (Lepidoptera, Notodontidae).J. Chem. Res. In press.
Midland, M. M. 1975. Preparation of monolithium acetylide in tetradedrofuran. Reaction with aldehydes and ketones.J. Org. Chem. 40:2250–2252.
Normant, J. F., andAlexakis, A. 1981. Carbometallation (C-alkylation) of alkynes: Stereo-specific synthesis of alkenyl derivatives.Synthesis 00:841–870.
Normant, J. F., Commerçon, A., andVillieras, J. 1975. Synthèse d'enynes et de diènes conjugués à l'aide d'organocuivreux vinyliques. Application à la synthèse du Bombykol.Tetrahedron Lett. 00:1465–1468.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Gardette, M., Alexakis, A. & Normant, J.F. Synthesis of (Z)-13-hexadecen-11-yn-1-yl acetate Major component of sex pheromone of the processionary moth. J Chem Ecol 9, 219–223 (1983). https://doi.org/10.1007/BF00988039
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00988039