SYNTHESIS OF OXYGENATED COMPOUNDS DERIVED FROM CARYOPHYLLENE

Studies of the chemical composition of clove oil indicate caryophyllen e epoxide and the presence of some other oxidation derivatives. To elu cidate these oxygenated compound structures, we have undertaken the sy nthesis of some caryophyllene oxide derivatives using 3-chloroperbenzo ic acid and caryophyllene. Caryophyllene epoxide, two diepoxides, a ke toepoxide and an aldehyde were isolated. Optimization of the procedure allowed us to selectively orient the reaction towards monoepoxides (1 00%), ketoepoxides (99%) or diepoxides (84%). The reduction of diepoxi des using lithium aluminium hydride led to two cyclic ether alcohols w ith tetrahydrofuranic and tetrahydropyranic rings, which were obtained in high yield and good regioselectivity. The structures of these comp ounds have been determinated from concerted application of two-dimensi onal NMR techniques.