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Synthesis 1995; 1995(6): 644-646
DOI: 10.1055/s-1995-3966
short paper
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Efficient Synthesis of the Aonidiella aurantii (Mask.) Sex Pheromone Component: (3S,6RS)-3-Methyl-6-(1-Methylethenyl)-9-decenyl Acetate

Panagiotis Kefalas, Nikitas Ragoussis*
  • *Vioryl S.A., Research Department, Kato Kifissia, GR-145-64, Greece, Fax +30(1)8074681
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Publication Date:
31 December 2000 (online)

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The title compound, active component of the sex pheromone of Aonidiella aurantii (California Red Scale), was synthesized in three steps starting from S-citronellyl acetate with a 30% overall yield. The key feature of the synthesis is a copper salt assisted, highly regioselective attack of the 4-butenyl bromide Grignard reagent on the γ-site of the chloroallylic system of (S)-8-chloro-3,7-dimethyl-6-octenyl acetate (8a).

regiospecific copper assisted Grignard C-alkylation of allylic chloride - pheromone synthesis