Metathesis-mediated synthesis of (R)-10-methyl-2-tridecanone, the southern corn rootworm pheromone |
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Authors: | Shikichi Yasumasa Mori Kenji |
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Institution: | Photosensitive Materials Research Center, Toyo Gosei Co, Ltd, Inzai, Chiba, Japan. |
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Abstract: | (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. |
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