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Title

General methodology for the synthesis of conjugated dienic insect sex pheromones

Authors
Gardette, M.
Jabri, N.
Normant, Jean F.
Published in Tetrahedron. 1984, vol. 40, no. 14, p. 2741-2750
Abstract 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 functionalised or non-functionalised lithium dialkyl cuprates, followed by the coupling of the resulting Z dialkenyl cuprates with functionalised or non-functionalised E or Z alkenyl iodides under Pd° catalysis. The following compounds were efficiently synthesized with a high degree of stereoisomeric purity: (E-Z)7, 9-dodecadien,-l-yl acetate 1 (Lobesia botrana), (E-Z)10, 12-hexadecadien,-l-ol 2 (Bombyx mori), (Z-E)9, 11-tetradecadien,-l-yl acetate 3 Spodoptera littoralis), (Z-E)5, 7-dodecadien-l-ol 4 (Malascoma disstria), (Z-Z)11, 13-Hexadecadien-l-al 5 (Amyelois transitella), (Z)9,ll-dodecadien-l-yl acetate 6 (Diparopsis castanea) and (Z-Z)9,11-tridecadien-l-yl acetate 22 (a known “pseudo-pheromone”).
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GARDETTE, M. et al. General methodology for the synthesis of conjugated dienic insect sex pheromones. In: Tetrahedron, 1984, vol. 40, n° 14, p. 2741-2750. https://archive-ouverte.unige.ch/unige:8165

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Deposited on : 2010-06-21

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