Russian Chemical Bulletin

, Volume 42, Issue 4, pp 760–763 | Cite as

Effective synthesis of femrrulactone II based on the use of 2-carhoxyethyltriphenylphosphonium bromide

  • B. A. Cheskis
  • N. A. Shpiro
  • A. M. Moiseenkov
Chemistry of Natural Compounds and Bioorganic Chemistry


A simple synthesis ofS,3Z-dodecen-11-olide, a component of the aggregation pheromone of the rusty grain beetleCryptolestes ferrugineus (Stephen), was developed. The key stage was Wittig olefination of C9-aldehyde, prepared fromS-propylene oxide, with C3-phosphorane generated from the title phosphonium salt.

Key words

ferrulactone II 2-carboxyethyltriphenylphosphonium bromide S-propylene oxide S-8-(2-tetrahydropyranyloxy)nonanal Wittig reaction stereochemistry 


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Copyright information

© Plenum Publishing Corporation 1994

Authors and Affiliations

  • B. A. Cheskis
    • 1
  • N. A. Shpiro
    • 1
  • A. M. Moiseenkov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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