Metathesis-mediated synthesis of (R)-10-methyl-2-tridecanone, the southern corn rootworm pheromone.
(R)-10-Methyl-2-tridecanone, the female sex pheromone of the southern corn rootworm (Diabrotica undecimpunctata howardi Barber), was synthesized in 9 steps from methyl (S)-3-hydroxy-2-methylpropanoate in a 15.7% overall yield. Olefin cross metathesis between (R)-6-methyl-1-nonene and 5-hexen-2-one employing Grubbs' first-generation catalyst was the key step of the synthesis.
Photosensitive Materials Research Center, Toyo Gosei Co, Ltd, Inzai, Chiba, Japan.
Yasumasa
Y
Shikichi
Kenji
K
Mori
D000818:Animals; D002384:Catalysis; D001517:Coleoptera / Q000737:chemistry*; D003432:Cross-Linking Reagents; D005260:Female; D007659:Ketones / Q000138:chemical synthesis*; D010675:Pheromones / Q000737:chemistry*; D003313:Zea mays / Q000469:parasitology*
D003432:Cross-Linking Reagents; D007659:Ketones; D010675:Pheromones; C009541:2-tridecanone