Protective group-free syntheses of (±)-frontalin, (±)-endo-brevicomin, (±)-exo-brevicomin, and (±)-3,4-dehydro-exo-brevicomin: racemic pheromones with a 6,8-dioxabicyclo〔3.2.1〕octane ring

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  • MORI Kenji
    Photosensitive Materials Research Center, Toyo Gosei Co., Ltd.

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  • Protective Group-Free Syntheses of (.+-.)-Frontalin, (.+-.)-endo-Brevicomin, (.+-.)-exo-Brevicomin, and (.+-.)-3,4-Dehydro-exo-brevicomin: Racemic Pheromones with a 6,8-Dioxabicyclo[3.2.1]octane Ring
  • Protective group free syntheses of plus-minus sign frontalin plus-minus sign endo brevicomin plus-minus sign exo brevicomin and plus-minus sign 3 4 dehydro exo brevicomin racemic pheromones with a 6 8 dioxabicyclo 3 2 1 octane ring
  • Protective Group-Free Syntheses of (±)-Frontalin, (±)-<i>endo</i>-Brevicomin, (±)-<i>exo</i>-Brevicomin, and (±)-3,4-Dehydro-<i>exo</i>-brevicomin: Racemic Pheromones with a 6,8-Dioxabicyclo[3.2.1]octane Ring

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Protective group-free syntheses of four racemic pheromones with a 6,8-dioxabicyclo[3.2.1]octane ring were achieved in five or six steps from commercially available (±)-3-butyn-2-ol (6) and 2-alkenyl halides or 2-alken-1-ol by employing Lewis acid-catalyzed acetalization of δ, ε-epoxy ketones as the key reaction. (±)-Frontalin (1) was prepared in a 25% overall yield in five steps from methallyl chloride (5a), (±)-endo-brevicomin (2) was prepared in a 23% overall yield in five steps from (E)-2-pentenyl bromide (5b), and (±)-exo-brevicomin (3) and (±)-3,4-dehydro-exo-brevicomin (4) were both prepared in a 4% overall yield in six steps based on (Z)-2-penten-1-ol (12).

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