Synthesis of an Alleged Constituent of New Brunswick Cranberry Leaves: The So-Called Cannivonine

An unambiguous ten-step synthesis of the compound possessing the reputed structure of the cranberry alkaloid cannivonine (1) is presented. Stereoselective reductive animation of the known cis-δ^5,6-2-octalone, protection of the nitrogen substituent, epoxidation, and N-deprotection with concomitant transannular ring closure provide a product possessing the desired 2-azatncyclo[5.3.1.0^3,8]undecane skeleton. Subsequent dehydration then yields the alleged cannivonine. Since the spectral data of the synthetic material fail to match those reported for cannivonine, a complete reinterpretation of the published data (and probably reisolation as well) and a reassignment of the structure of cannivonine appear to be in order.