SYNTHESES OF SESQUITERPENE EPOXIDES AND ALCOHOLS FROM GAMMA-GURJUNENE

Citation
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
Citations number
12
Categorie Soggetti
Food Science & Tenology",Agriculture,"Chemistry Applied
ISSN journal
00218561
Volume
45
Issue
1
Year of publication
1997
Pages
221 - 226
Database
ISI
SICI code
0021-8561(1997)45:1<221:SOSEAA>2.0.ZU;2-D
Abstract
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.