ChemInform Abstract: Synthesis of Z-Isomeric Insect Sex Pheromone Components via Ethenolysis of 1,5-Cyclooctadiene

A novel syntheses of Z-5-decenol, Z-5-decenyl acetate, Z-7-dodecenol, Z-7-dodecenyl acetate, Z-9-tricosene, Z-7,8-epoxy-2-methyloctadecane which are sex pheromone components of Lepidoptera and Diptera orders, have been realized via stereoselective cometathesis of 1,5-cyclooctadiene with ethylene in the presence of MoCl 5 /SiO 2 -SnMe 4 as a key reaction. The main cometathesis product, 1,Z-5,9-decatriene, has been converted into pheromone components mentioned above by regioselective partial hydroboration or hydrozirconation with help of 9-BBN and Cp 2 ZrHCl, correspondingly. The protonolysis of the obtained zirconosene derivative gave 1,Z-5-decadiene. Hydroboration-oxidation or hydroboration-C 2 -homologation of the latter led to Z-5- or Z-7 monoene pheromone components. Hydroboration-iodination of terminal double bond in 1,Z-5,9-decatriene, and further cross-coupling of the obtained iodine derivative with convenient lithium cuprates resulted in Z-9-tricosene, the main sex pheromone component of House Fly ( Musca Domestica ), or in 2-methyl-Z-7-octadecene, the precursor of Gypsy Moth ( Lymantria Dispar ) sex attractant.