The synthesis of a phenolic sesquiterpene isolated from <i>Elvira bifora</i> (Compositae)

Abstract

The proposed structure for a phenolic sesquiterpene, 2-(11,5?- dimethylhex-4?-enyl)-4-methylphenol (1), previously isolated from Elvira biflora, has been confirmed by synthesis of its racemate in 3 steps from 3-bromo-4-methoxytoluene and 6-methylhept-5-en-2-one. A structural isomer, 4-(1?,5?-di-methylhex-4?-enyl)-2-methylphenol (4), has also been synthesized for spectral comparison, since the natural product and the synthetic racemate (1) were only able to be compared by N.M.R. spectroscopy.