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General methodology for the synthesis of conjugated dienic insect sex pheromones



General methodology for the synthesis of conjugated dienic insect sex pheromones



Tetrahedron 40(14): 2741-2750



A general methodology for the synthesis of various types of dienic insect sex pheromones (Z-E, E-Z, Z-Z) is based on the carbocupration of acetylene by functionalized or non-functionalized lithium dialkyl cuprates, followed by the coupling of the resulting Z dialkenyl cuprates with functionalized or non-functionalized E or alkenyl iodides under Pd.degree. catalysis. The following compounds were efficiently synthesized with a high degree of stereoisomeric purity; (E-Z)7,9-dodecadien-1-yl acetate (Lobesia botrana), (E-Z)10,12-hexadecadien-1-ol (Bombyx mori), (Z-E)9,11-tetradecadien-1-yl acetate Spodoptera littoralis), (Z-E)5,7-dodecadien-1-ol (Malacosoma disstria), (Z-Z)11,13-hexadecadien-1-al (Amyelois transitella), (Z)9,11-dodecadien-1-yl acetate (Diparopsis castanea) and (Z-Z)9,11-tridecadien-1-yl acetate 22 (a known "pseudo-pheromone").

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Accession: 005508794

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DOI: 10.1016/s0040-4020(01)96893-0



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