New Approach to the Synthesis of Pheromones and Juvenoids with Small Cycles in Molecule
Natural terpenes (+)-3-carene and α-pinene are widely used in the synthesis of biologically active substances. On the basis of the products of their ozonolytic splitting, synthesis schemes were developed for juvenoids, pheromones, pyrethroids. In the present work we propose a new efficient approach to the synthesis of pheromones and juvenoids with cyclopropane and cyclobutane rings in the molecule by means of ozonation of α,β-unsaturated ketones carenone and verbenone, which are easily obtained from (+)-3-carene and α-pinene. The mechanism of formation of 2,2-dimethyl-3-acetylcyclobutanecarboxylic acid - synton is the synthesis of the pheromone of grape mealybugs - is proposed.