Przemysl Chemiczny, Vol.88, No.5, 557-562, 2009
Lactones Part XXXIII1). Synthesis and antifeedant activity of alkyl substituted epsilon-lactones
The Baeyer-Villiger oxidn. of some Me, Me-2 and Me-3 substituted cyclohexanones with m-ClC6H4COOH afforded resp. e-lactones. Unsatd. terpenoid ketones: (-)-verbenone and (+)-dihydrocarvone were oxidized under the same conditions to mixts. of resp. epoxyketones and epoxy-e-lactones. The products were isolated by column chromatog., identified by NMR and IR spectroscopy and tested for antifeedant activity against the adults of the grain weevil, the adults and larvae of the confused flour beetle and the larvae of the khapra beetle. The epoxylactone obtained from (-)-verbenone showed the highest antifeedant activity against the adults of grain weevil (Sitophilus granaries, L.).