60479-10-9Relevant articles and documents
Synthesis of oxygenated compounds derived from caryophyllene.
Bombarda, Isabelle,Gaydou, Emile M.,Smadja, Jacqueline,Faure, Robert
, p. 836 - 842 (2007/10/02)
Studies of the chemical composition of clove oil indicate caryophyllene epoxide and the presence of some other oxidation derivatives.To elucidate these oxygenated compound structures, we have undertaken the synthesis of some caryophyllene oxide derivatives using 3-chloroperbenzoic acid and caryophyllene.Caryophyllene epoxide, two diepoxides, a ketoepoxide and an aldehyde were isolated.Optimization of the procedure allowed us to selectively orient the reaction towards monoepoxides (100percent), ketoepoxides (99percent) or diepoxides (84percent).The reduction of diepoxides using lithium aluminium hydride led to two cyclic ether alcohols with tetrahydrofuranic and tetrahydropyranic rings, which were obtained in high yield and good regioselectivity.The structures of these compounds have been determined from concerted application of two-dimensional NMR techniques. - Key words: oxidation; reduction; caryophyllene; epoxide; diepoxide; ether alcohol; intramolecular cyclization