STEREOCHEMISTRY OF EPOXIDATION OF SOME CARYOPHYLLENOLS

Epoxidation of the caryophyllene allylic alcohols 3-5 by tert-butyl hy droperoxide/vanadyl acetylacetonate afforded the epoxides 6a, 7, and 8 , respectively. The tetracyanoethylene-catalyzed solvolysis shed some light on the stereochemistry of epoxidation. Formation oi. trans epoxi des by syn epoxidation is a consequence of the conformational flexibil ity of the nine-membered ring, which places the alcohol at C-5 close t o the alpha-face of the elzdo-alkene in 4 and close to the beta-face i n 3 and 5.