- Preparation of Four Geometric Isomers of (11E)-4,6,11-Hexadecatrienal and Their Effect toward Male Eri-Silk Moths
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Four geometric isomers of (11E)-4,6,11-hexadecatrienal were prepared, and their pheromone activity towards male eri-silk moths was evaluated.The EAG activity of each isomer was determined by the EAG-GLC method in order of increasing activity to be (4Z,6E,
- Tomida, Ichiro,Fuse, Takao
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p. 1760 - 1762
(2007/10/02)
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Coupling reactions of lithium compounds, (Z)-carbonyl olefination of phosphonium ylides and 'crossed' Wittig olefination of bisylides are the key reaction steps in the synthesis principle for nonconjugated, bisolefinic Lepidoptera pheromones and structural analogs. Double unsaturated (E,Z)- and (E,E)-1-vinyl halides are converted into the corresponding (E,Z)- and (E,E)-1-vinyl lithium compounds and coupled selectively to (E,Z)- and (E,E)-alkadienols, alkadienals and alkadienyl acetates with different carbon chain length, geometry and relative positions of double bonds. 'Crossed' Wittig reactions of 1,ω-alkylidene bisylides with two different alkanals gives rise to the formation of corresponding (Z,Z)-dienic sex attractants and derivatives. A monounsaturated (E)-1-vinyl iodide is the synthon for the preparation of an (E)-alkenyl bromide which is converted to an (E)-alkenyl phosphonium salt and (Z)-selectively olefinated to (Z,E)-isomers of moth sex pheromones.
- Bestmann,Zeibig,Vostrowsky
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p. 1039 - 1047
(2007/10/02)
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