Chemical and microbiological oxidation of (-)-cis-carane-4-one leading to chiral compounds and evaluation of their antifeedant activity

Abstract

Starting from (+)-3-carene 1, naturally occurring bicyclic, monoterpene hydrocarbon, (-)-cis- carane-4-one 3 was obtained as a result of the two-step synthesis. Our investigations were focused on the optimization of chemical Baeyer-Villiger reaction of 3 leading to å-lactones. A mixture of terpenoid lactones 4a, 4b was obtained and next separated using column chromatography. The pure compounds were subjected to the evaluation of antifeedant activity towards three species of storage insects. Fusarium culmorum, Fusarium oxysporum and Aspergillus niger were chosen among six fungal strains to perform microbiological Baeyer- Villiger oxidation. As a result, three derivatives were isolated and characterized by spectroscopic methods. ©ARKAT-USA, Inc.