Pheromone Synthesis, CCVIII: Synthesis of (1S,3S,7R)-3-Methyl-α-himachalene, the Sex Pheromone of the Sandfly Lutzomyia longipalpis from Jacobina, Brazil

All articles of this category (1 S ,3 S ,7 R )-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 (1 R ,7 R )-α-himachalene of plant origin. asymmetric synthesis - Diels-Alder reactions - Lutzomyia longipalpis - pheromones - terpenoids