I. Bombarda et al., SYNTHESES OF SESQUITERPENE EPOXIDES AND ALCOHOLS FROM GAMMA-GURJUNENE, Journal of agricultural and food chemistry, 45(1), 1997, pp. 221-226
gamma-Gurjunene, a natural sesquiterpene isolated from gurjun balsam,
is obtained by isomerization of alpha-gurjunene in acidic medium. Oxid
ation of gamma-gurjunene by reaction with m-chloroperbenzoic acid yiel
ded a mixture of two monoepoxides and two diepoxides. Reduction reacti
on of a mixture of diepoxides with 4 equiv of lithium aluminum hydride
or lithium triethylborohydride allowed isolation of a single diol in
93% yield. Four diols were obtained when reduction was realized with 2
equiv of reducing agent, including an epoxy alcohol, two enediols, an
d a dienol. The structure formulas of the compounds were determinated
using one- and two-dimensional NMR and gas chromatography-mass spectro
metry.