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
スポンサーリンク
概要
- 論文の詳細を見る
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).
- 2011-05-23
著者
関連論文
- Molecular Action Mode of Hippospongic Acid A, an Inhibitor of Gastrulation of Starfish Embryos
- Improved Synthesis of Three Methyl-Branched Pheromone Components Produced by the Female Lichen Moth
- New Synthesis of (11Z,13Z)-11,13-Hexadecadienal, the Female Sex Pheromone of the Navel Orangeworm
- First Synthesis of (±)-Basidifferquinone C, an Inducer for Fruiting-Body Formation in Polyporus arcularius
- 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
- New Syntheses of 1,7-Dimethylnonyl Propanoate, the Western Corn Rootworm Pheromone, in Four Different Ways via Cross Metathesis, Alkylation and Coupling Reactions
- Metathesis-Mediated Synthesis of (R)-10-Methyl-2-tridecanone, the Southern Corn Rootworm Pheromone
- Synthesis of (1R,7Z)-1-Methyl-7-hexadecenyl Acetate, the Female Sex Pheromone of the Honey Locust Gall Midge
- Synthesis of (1R,7Z)-1-Methyl-7-hexadecenyl Acetate, the Female Sex Pheromone of the Honey Locust Gall Midge
- Synthesis and Bioassay of the Eight Analogues of the CH503 Male Pheromone (3-Acetoxy-11,19-octacosadien-1-ol) of the Drosophila melanogaster Fruit Fly
- Synthesis of All the Stereoisomers of 6-Methyl-2-octadecanone, 14-Methyl-2-octadecanone, and 6,14-Dimethyl-2-octadecanone, Sex Pheromone Components of the Lyclene dharma dharma Moth, from the Enantiomers of Citronellal