Abstract A range of 2-substituted perhydrofuro [2, 3-b] furans have been synthesized in a stereoselective manner through a sequence involving the Lewis-acid catalyzed carbonyl- ene reaction of a protected isopentenyl alcohol with a variety of enophiles, deprotection of the corresponding monoprotected diols, and palladium-catalyzed intramolecular acetalization under Wacker-type reaction conditions.