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Synthesis 1999; 1999(5): 783-786
DOI: 10.1055/s-1999-3467
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Syntheses of Both Enantiomers of 1,7-Dioxaspiro[5.5]undecane: Pheromone Components of the Olive Fruit-Fly Dacus oleae from a New Chiral Intermediate, the (S S)-2-(p-Tolylsulfinyl)prop-2-en-1-ol

Patricia Hayes* , Christian Maignan
  • *Laboratoire de Synthèse Organique (associé au CNRS), Faculté des Sciences, Avenue Olivier Messiaen, F-72085 Cedex 9, Le Mans, France; Fax +33(2)43 83 39 02; E-mail: maignan@aviion.univ-lemans.fr
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Publication Date:
31 December 1999 (online)

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Both enantiomers of 1,7-dioxaspiro[5.5]undecane, the pheromone components of the olive fruit-fly Dacus oleae have been synthesized from a new chiral sulfoxide, (S S)-2-(p-tolylsulfinyl)prop-2-en-1-ol via hetero Diels-Alder reaction, chromatographic separation of the diastereomers on a silica gel column and desulfurization over Raney nickel as key steps.

insect pheromone - hetero Diels-Alder reaction - chiral 1,7-dioxaspiro[5.5]undecane - chiral sulfinyl heterodiene - (S S)-2-(p-tolylsulfinyl)prop-2-en-1-ol