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Synthesis 1991; 1991(12): 1231-1235
DOI: 10.1055/s-1991-28425
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Cyclische Ether als Edukte zur Synthese von Schmetterlings-Pheromonen

Helmut Poleschner* , Matthias Heydenreich, Dieter Martin
  • *Biologische Zentralanstalt Berlin, Stahnsdorfer Damm 81, D/O-1532 Kleinmachnow, Germany
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Publication Date:
29 April 2002 (online)

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Cyclic Ethers as Educts for the Synthesis of Lepidoptera Pheromones ω-Iodo(trialkylsiloxy)alkanes 2 prepared by ring opening of cyclic ethers with iodotrimethylsilane, are useful starting materials for the synthesis of pheromone components. Reaction with triphenylphosphine to give the corresponding Wittig reagent and subsequent coupling with lithium (Z)-dihex-1-enylcuprate gives (Z)-alken-1-ols 5 and 7, after deprotection, in good yields. The direct coupling of 2 with alkynes failed because of competition reactions, however, the more stable ω-iodo-1-(tert-butyldimethylsiloxy)alkanes were able to undergo C,C-coupling with alkynes. The thus formed 1-(tert-butyldimethylsiloxy)-5-decyne (13c) was hydrogenated and deprotected to give (E)-5-decen-1-ol (15c).

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