Hydration and Lead Tetraacetate-Oxidation of a Mixture of δ-and γ-Elemene

Abstract

Hydration and lead tetraacetate-oxidation of a mixture of δ- and 7-elemene ([1] and [2])were investigated. By hydration of a mixture of [1]and [2]with trichloroacetic acid, elemol [3] was obtained in high selectivity. A novel compound, c-3-isopropeny1-1-isopropyl4-methyl-t-4-vinyl-γ-1-cyclohexanol4was accompanied as a minor product. The configuration of hydroxyl group of [4] was confirmed by the variation in the contact shift of each proton using the shift reagent, Eu (dpm)³.Oxidation of a mixture of [1]and [2]with lead tetraacetate and subsquent hydrolysis gave 1-methy1-1-viny1-2-isopropenyl-4-(1-methyl-2-hydroxyethylidene)cyclohexane [5 a] and 1-methyl-1-vinyl-2-isopropenyl-4- (1-methyl-1, 2-dihydroxyethyl)cyclohexane [6a] which are new sesquiterpenoids. All of the compounds were found to possess a mild wood like odor.