Synthesis of 9Z,11E;13-Tetradecatrienal, the Major Component of the Sex Pheromone of the Carob Moth,Ectomyelois ceratoniae(Lepidoptera: Pyralidae).

Abstract

9Z,IlE,13-Tetradecatrienal, a component of the sex pheromone of the carob moth, was synthesized by a short and efficient ronte, with a high degree of stereoselectivity. Key steps included the Pd-catalyzed construction of a conjugated dienynol intermediate from E-I,2-dichloroethylene, and stereo-and regiospecific reduction of the dienynol with activated zinc in aqueous alcohol.

The First Practical Synthesis of (S)-Pyrethrolone, an Alcohol Moiety of Natural Pyrethrins I and II

“…Evaporation of the solvent followed by purification by chromatography on Florisil (diethyl ether/n-hexane=I/1) gave 4.3g (85.0%) of (S)-( + )-pyrethrolone; n~1. 5 …”

“…Finally, clean semihydrogenation of the triple bond in 8 was achieved by use of activated Zn in l-propanoI 5 ) at 100°C for 30 h, giving pure (S)-pyrethrolone in 85% yield * To whom correspondence should be addressed. ( Fig.…”

“…Although several papers2) describe syntheses of pyrethrolone, including the optically active (S)-isomer (3), these involve multistep routes that require ketone protection, and also lead to pyrethrolone contaminated with the (E)-isomer (5). An example of the reported conversion of (S)-allethrolone (4) to (S)-pyrethrolone is pictured in Fig.…”

Comparative study of the sex pheromone of carob moth, Apomyelois ceratoniae (Zeller, 1839) (Lepidoptera: Pyralidae) from four regions of Iran using headspace solid phase micro extraction - gas chromatography/mass spectrometry

“…(Z,E)-9,11,13-tetradecatrienal was synthesized (Figure 1) by modification of the method of Millar (1990). Tetrahydrofuran (THF) was distilled from sodium/benzophenone ketyl under N 2 .…”

“…Populations of A. ceratoniae were sampled form four regions of Iran, viz. Isfahan, Sistan, Lorestan and South Khorasan, and volatile substances emitted by virgin females collected, analyzed and compared them to a reference samples (Millar, 1990, Baker et al, 1991.…”