Abstract
The total synthesis of the sesquiterpene (+)-longifolene (1) by an intramolecular Diels-Alder cycloaddition strategy is described. Addition of methyllithium to the epoxyfulvene 13, derived from cyclopentadiene and 3,4-epoxy-2-butanone, led to an exo-tet cyclization of the resulting cyclopentadienyl anion to generate the spiro[2.4]hepta-4,6-diene alcohol 14. Resolution of this material was effected via its menthyl carbonate derivative 15. Oxidation of the (+)-R-alcohol with active MnO 2 afforded the cyclopropyl aldehyde 16 which was condensed with the anion derived from methyl 3-methylcrotonate in the presence of cadmium chloride to generate an unsaturated lactone or an unsaturated ester
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