Telomers of 1,3-Butadiene With Water and Carbon Oxide in Directed Synthesis of Insect’s Pheromones

Abstract

Insect pheromones fit well into the modern concept of integrated plant protection, the main purpose of which is not the complete destruction of insect pests, but the management of their number without affecting or affecting to a minimum extent all other organisms in the biocenosis. Since pheromones are produced in insect organisms most often in nanogram quantities, the only way to obtain them for practical purposes is through multi-stage chemical synthesis. In connection with the achievements of metal complex catalysis, a number of oligomers, co-oligomers, and telomeres of lower 1,3-dienes of regular structure became available, therefore, the study of the chemo-, stereo-, and regioselective pathways for the conversion of these substrates into practically important low-molecular insect bioregulators is relevant. The author’s review presents the results of studies of the laboratory of insect bioregulators of the Ufa Institute of Chemistry of the Ufa Scientific Center of the Russian Academy of Sciences on the use of available synthetic telomeres of 1,3-butadiene with water and carbon monoxide – 2E,7-octadiene-1-ol and isopropyl-3E,8-nonadienoate, respectively, with E-stereoisomeric purity of not less than 98% in the directed synthesis of mono- and diene components of the acetogenin and macrolide structure of a number of pheromones of economically important harmful insects of the orders Lepidoptera and Coleoptera (sex pheromone of Mediterranean fruit fly Ceratitis capitata, fruit-tree leafroller moth Archips argyrospilus and meadow moth Loxostege sticticalis, Hessian fly Mayetiola destructor, beet moth Scrobipalpa ocellatella, European grapevine moth Lobesia botrana, of females lackey moth Malocosoma neustra L., silkworm Bombyx mori, currant borer moths Synanthedon tipuliformis and wood leopard moth Zeuzera pyrina, the melon fly Dacus cucurbitae, the peach twig borer moths Anarsia lineatella, the turnip moth Agrotis segetum) and 9-oxo-2E-decenoic acid – the multifunctional queen pheromone of the honeybee Apis mellifera L., using at key stages reactions of hydride reduction, hydroboration- or hydroalumination-oxidation, catalyzed cross-coupling, Wittig olefination, etc.