SYNTHESIS OF PHEROMONE DERIVATIVES VIA Z-SELECTIVE OLEFIN METATHESIS
Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.
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Paragraph 0248-0249; 0252
(2021/12/28)
Copper-catalyzed cross-coupling of (Z)-allyl phenyl ethers with Grignard compounds in the synthesis of insect pheromones
(8Z)-Dodec-8-en-1-yl acetate (pheromone of oriental fruit moth Grapholita molesta) and (9Z)-dodec-9-en-1-yl acetate (pheromone of grape berry moth Paralobesia viteana) containing impurities of isomeric structures were synthesized via copper-catalyzed cross-coupling of (Z)-1-phenoxyhex-2-ene and (Z)-1-phenoxypent-2-ene, respectively, with Grignard compounds in the key stage.
Petrushkina,Kalinin
experimental part
p. 1897 - 1899
(2009/02/08)
Syntheses of the Sex Pheromone of the European Pine Shoot Moth (Rhyacionia buoliana). The Grignard Route
Grignard-Kopplungen zwischen zwei entsprechenden Synthonen fuehren zum (E)-9-Dodecen-1-ylacetat (1), dem Sexuallockstoff des Kiefernknospentriebwicklers (Rhyacionioa buoliana).Als solche Synthon-Paare wurden 1-Brom-(E)-2-penten (2) und 7-Bromheptyltetrahydropyranylether (3) bzw. (E)-3-Hexen-1-yltosylat (4) und 6-Bromhexyltrimethylsilylether (5) eingesetzt.Das Endprodukt (1) und die wichtigsten Zwischenprodukte wurden durch ihre 1H- und 13C-NMR-Spektren charakterisiert.Durch die zweite Synthese wurden 100percent Regio- und 99percent Stereoselektivitaet erreicht.
Popovici, N.,Botar, A. A.,Barabas, A.,Oprean, I.,Hodosan, F.
p. 17 - 26
(2007/10/02)
METATHESE D'ACETATES D'ALCOOLS ω-INSATURES. SYNTHESE DE PHEROMONES D'INSECTES
Esters of alkenoic acids, including insect pheromones as examples, have been synthesized using alkene metathesis reactions.
Levisalles, Jaques,Villemin, Didier
p. 3181 - 3186
(2007/10/02)
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