109987-11-3Relevant academic research and scientific papers
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
Mori, Kenji
, p. 976 - 981 (2012/01/05)
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).
APPLICATION OF THE CARBONYL EPOXIDE REARRANGEMENT TO THE FORMATION OF DIOXABICYCLOALKANES AND ALKENES. SYNTHESIS OF THE MUS MUSCULUS PHEROMONE
Wasserman, Harry H.,Wolff, Steven,Oku, Teruo
, p. 4909 - 4912 (2007/10/02)
Acid-catalyzed intramolecular opening of epoxides by carbonyl groups provides a general stereocontrolled method for forming dioxabicyclo systems, including the (+/-)-Mus musculus pheromone and products corresponding to certain insect pheromones.
