Studies in relation to biosynthesis. XL. Some aspects of the chemistry of o-isopentenylphenols and related compouncls

Abstract

Several 2,2-dimethylchromene derivatives, including the natural flavonoids scandenin and lonchocarpic acid, have been reduced by lithium in ammonia to o-isopentenylphenols. Several hydroxyisopropyldihydrobenzofurans can similarly be reduced, and one was converted by reaction with N-bromosuccinimide into a benzofuran derivative lacking the isopropyl group. Alkylations of catechol and aesculetin with isoprene dibromide were examined, and in the latter case resulted in what is probably (±)-obliquin.