Stereospecific syntheses of sex pheromones of the californian red scale and white peach scale (Homoptera:Diaspididae) based on 1,4-cis-hydrogenation of dienes |
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Authors: | A. A. Vasil'ev A. L. Vlasyuk G. V. Kryshtal E. P. Serebryakov |
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Affiliation: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp, 117913 Moscow, Russian Federation;(2) The Higher Chemical College, Russian Academy of Sciences, 9 Miusskaya pl, 125047 Moscow, Russian Federation |
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Abstract: | Stereospecific syntheses of (±)-3-methyl-6-isopropenyl-3(Z),9-decadien-1-yl acetate and (±)-3,9-dimethyl-6-isopropenyl-3(Z),9-decadien-1-yl propionate (the Racemoc forms of the pheromones of the scalesAonidiella aurantii andPseudaulascaspis pentagona) with a geometrical purity of the (Z)-trisubstituted double bond not lower than 99 % were performed. The key step in both syntheses was the 1,4-cis-hydrogenation of the corresponding ethyl 3-methyl-6-(1, 1-ethylenedioxyethyl)-2,4,9-decatrienoates catalyzed with chromium carbonyl complexes. These 2,4-dienes were obtained in five conventional steps including the alkylation of ethyl acetoacetate by the appropriate 1-bromo-3-butenes and the Horner-Emmons olefination of the corresponding -branched aldehydes.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2026–2031, October, 1995. |
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Keywords: | (± )-3-methyl-6-isopropenyl-3(Z),9-decadien-1-yl acetate, (± )-3,9-dimethyl-6-isopropenyl-3(Z),9-decadien-1-yl propionate, synthesis aldehydoketals ethyl 2,4-alkadi-enoates, 1,4-cis-hydrogenation the Horner-Emmons olefination ethyl acetoacetate, alkylation arene chromium tricarbonyl complexes |
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