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Synthesis of Germacrene-B and Its Extension to the Synthesis of (±)-9-Methylgermacrene-B, the Racemate of the Male-Produced Sex Pheromone of the Sandfly Lutzomyia longipalpis from Lapinha, Brazil

✍ Scribed by Shin-etsu Muto; Yutaka Nishimura; Kenji Mori

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
235 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

Both germacrene-B (2) and 9-methylgermacrene-B [(±)-1]

shown to be the racemate of the male-produced sex pheromone of the sandfly Lutzomyia longipalpis from were synthesized by employing cyclization reactions [8 Ǟ 9 and (±)-20 Ǟ (±)-21] as the key steps. The latter [(±)-1] was Lapinha, Brazil.

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✍ Satoshi Sano; Kenji Mori 📂 Article 📅 1999 🏛 John Wiley and Sons 🌐 English ⚖ 337 KB

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