Stereoselective synthesis of some isomers of dodecadien-1-ol: Compounds related to the pine moth sex pheromone.

AND, Tetsu; Vu, Manh Huynh; Yoshida, Shigeo; Takahashi, Noriko

doi:10.1271/bbb1961.46.717

Cited by 7 publications

(1 citation statement)

References 1 publication

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“…This route seemed attractive due to the availability of starting (E)-7-dodecen-5-yn-1-ol through the palladium-catalyzed alkylation of tetrahydro-2-(5hexynyloxy)-2H-pyran with (E)-1-iodo-1-hexene (6). Ando et al (6) reported that Lindlar reduction of (E)-7-dodecen-5-yn-1-ol lacked selectivity, providing a mixture of (Z,E)-diene and monoenic compounds from which the desired product was isolated by chromatography on silica impregnated with silver nitrate. Stille and Simpson (7) used hydroboration of the protected (E)-7-dodecen-5-yn-1-ol to achieve high yield and purity of the pheromone.…”

Section: Introductionmentioning

confidence: 99%

Syntheses of (Z,E)-5,7-Dodecadienol and (E,Z)-10,12-Hexadecadienol, Lepidoptera Pheromone Components, via Zinc Reduction of Enyne Precursors. Test of Pheromone Efficacy against the Siberian Moth

Khrimian

Klun

Baranchikov

et al. 2002

J. Agric. Food Chem.

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Efficient syntheses of (Z,E)-5,7-dodecadienol, a pheromone component of the Siberian moth, Dendrolimus superans sibiricus, and (E,Z)-10,12-hexadecadienol, a pheromone component of various Lepidoptera pheromones, were accomplished by cis reduction of the corresponding enynols with activated zinc. The most energetic reagent was zinc galvanized with copper and silver (Zn/Cu/Ag) that achieved rapid and high-yield reduction in methanol-water. The stereoselectivity of semi-hydrogenation was > or =98%. A process whereby zinc dust was continuously activated throughout the reduction with an acid was also satisfactory (95-98% cis). Field evaluation of the 1:1 mixture of (Z,E)-5,7-dodecadienol and (Z,E)-5,7-dodecadienal with the Siberian moth in Russia showed that the rubber septa pretreated with compound and stored at -80 degrees C were as effective as freshly treated septa. Moth responses to septa aged in open air indicated that lure effectiveness declined significantly after 2 weeks of aging. Thus, if rubber septa are used as pheromone dispensers in Siberian moth traps monitoring, they should be replaced biweekly with fresh septa for optimal trap effectiveness.

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Section: Introductionmentioning

confidence: 99%

Syntheses of (Z,E)-5,7-Dodecadienol and (E,Z)-10,12-Hexadecadienol, Lepidoptera Pheromone Components, via Zinc Reduction of Enyne Precursors. Test of Pheromone Efficacy against the Siberian Moth

Khrimian

Klun

Baranchikov

et al. 2002

J. Agric. Food Chem.

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New and Simple Syntheses of the Attractants of the Female Melon Fly, Dacus cucurbitae

Yen

Chen

1999

J Chinese Chemical Soc

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The attractant of the female melon fly, (E)-6-nonenyl acetate, and the two analogs, (E)-7-dodecenyl acetate and (E)-7-decenyl acetate were synthesized via hydrozirconation to control the regioselective coupling reactions and resulted in good yields.(7)8 in 98% yield, by treatment with 2,3-dihydropyran and lithium acetylide-ethylenediamine complex in dimethyl sulfoxide (DMSO). Hydrozirconation" of alkynes 6 and 7 with (CsHshZr(H)CI and h, gave (E)-7-iodo-l-(2-tetrahydropyranyloxyj-o-heptene (8) in 74% yield and (E)-8-iodo-1-(2-tetrabydropyranyloxy).7-octene (9) in 71% yield. The iodides 8 and 9 were then coupled with either ethylmagnesium bromide or butylmagnesium bromide in the presence of tetrakis(triphenylphosphine)-palladium lPd(PPb3)4] as a catalyst to give (E)-1-(2-tetrahydropyranyloxy)-6-nonene (10),10 in 71 % yield, (E)-1-(2-tetrahydropyranyloxy)-7-decene nn" and (E)-1-(2-tetrahydropyranyloxy)-7-dodecene

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Effects of double-bond configuration on interaction between a moth sex pheromone component and its receptor

1987

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The dependence of the electrophysiological activity on the change of double-bond configuration of (Z)-5-decenyl acetate, a pheromone component of the turnip moth,Agrotis segetum, and a dienic analog, (E)-2,(Z)-5-decadienyl acetate, have been investigated by single-cell measurements and molecular mechanics calculations (MM2). A previously reported model for the interaction between a moth sex pheromone component and its receptor has been refined. This new model gives an essentially quantitative correlation between the measured activities and the calculated conformational energies for a biologically active conformation defined by the model. Previously obtained structure-activity results for chain-elongated analogs of (Z)-5-decenyl acetate are significantly improved by the refined model. The effect of a change of the double-bond configuration on the substrate-receptor interaction is not additive but depends on the conformational properties of the entire molecule.

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Stereoselective synthesis of some isomers of dodecadien-1-ol: Compounds related to the pine moth sex pheromone.

Cited by 7 publications

References 1 publication

Syntheses of (Z,E)-5,7-Dodecadienol and (E,Z)-10,12-Hexadecadienol, Lepidoptera Pheromone Components, via Zinc Reduction of Enyne Precursors. Test of Pheromone Efficacy against the Siberian Moth

Syntheses of (Z,E)-5,7-Dodecadienol and (E,Z)-10,12-Hexadecadienol, Lepidoptera Pheromone Components, via Zinc Reduction of Enyne Precursors. Test of Pheromone Efficacy against the Siberian Moth

New and Simple Syntheses of the Attractants of the Female Melon Fly, Dacus cucurbitae

Effects of double-bond configuration on interaction between a moth sex pheromone component and its receptor

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