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Enantioselective synthesis of (1S,3S,7R)-3-methyl-α-himachalene, the sex pheromone of the sandfly Lutzomyia longipalpis from Jacobina, Brazil

✍ Scribed by Kenji Mori; Takuya Tashiro; Satoshi Sano

Book ID
104210510
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
153 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

1S,3S,7R)-3-Methyl-a-himachalene, the sex pheromone of the male sand¯y (Lutzomyia longipalpis) from Jacobina, Brazil, was synthesized enantioselectively by employing Evans' or Oppolzer's asymmetric methylation as the key step. The absolute con®guration at the ring junction of this pheromone is opposite to that of the known (1R,7R)-a-himachalene of plant origin.

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Four stereoisomers (1a-d) of (±)-3-methyl-α-himachalene produced sex pheromone of the sandfly Lutzomyia longipalpis was shown to possess the structure and relative were synthesized by employing the intramolecular Diels-Alder reaction of (±)-14 to (±)-18 as the key-step. The male-configuration as dep

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