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Synthesis 2000; 2000(13): 1852-1862
DOI: 10.1055/s-2000-8220
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Pheromone Synthesis, CCVIII: Synthesis of (1S,3S,7R)-3-Methyl-α-himachalene, the Sex Pheromone of the Sandfly Lutzomyia longipalpis from Jacobina, Brazil

Takuya Tashiro* , Masahiko Bando, Kenji Mori
  • *Department of Chemistry, Faculty of Science, Science University of Tokyo, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan; Fax + 81(3)32 35 22 14; E-mail: htakikaw@ch.kagu.sut.ac.jp
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Publication Date:
31 December 2000 (online)

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(1S,3S,7R)-3-Methyl-α-himachalene, the sex pheromone of the male sandfly (Lutzomyia longipalpis) from Jacobina, Brazil, was synthesized enantioselectively by employing Evan's or Oppolzer's asymmetric methylation and intramolecular Diels-Alder reaction as the two key steps. The absolute configuration of the product was unambiguously established by X-ray analysis of a compound related to one of the synthetic intermediates. The ring junction of this sandfly pheromone possesses the absolute configuration opposite to that of the known (1R,7R)-α-himachalene of plant origin.

asymmetric synthesis - Diels-Alder reactions - Lutzomyia longipalpis - pheromones - terpenoids

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