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Russian Chemical Bulletin

, Volume 44, Issue 10, pp 1946–1951 | Cite as

Stereospecific syntheses of sex pheromones of the californian red scale and white peach scale (Homoptera:Diaspididae) based on 1,4-cis-hydrogenation of dienes

  • A. A. Vasil'ev
  • A. L. Vlasyuk
  • G. V. Kryshtal
  • E. P. Serebryakov
Chemistry of Natural Compounds and Bioorganic Chemistry

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 α-branched aldehydes.

Key words

(±)-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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Copyright information

© Plenum Publishing Corporation 1995

Authors and Affiliations

  • A. A. Vasil'ev
    • 1
  • A. L. Vlasyuk
    • 2
  • G. V. Kryshtal
    • 1
  • E. P. Serebryakov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.The Higher Chemical CollegeRussian Academy of SciencesMoscowRussian Federation

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