Enantioselective approach to 7-azabicyclo[2.21lheptane ring systems using D-(-)quinic acid as the chiral educt: Application to the formal synthesis of (+)-epibatidine

Article abstract of DOI:10.1016/S0040-4039(96)02391-X

By utilizing, D-(-)-quinic acid as the chiral starting material the optically pure 7-[(1,1-dimethylethoxy)carbonyl]-7-azabicyclo[ 2.2.1]heptan-2-one 2, an advanced intermediate already taken to (+)-epibatidine 1, a non-opioid analgesic isolated from Ecuadorian poison frogs, was synthetized through a facile, regioselective intramolecular nucleophilic ring opening of a cyclic sulfate moiety.