SYNTHESIS OF (-N-BOC-7-AZABICYCLO[2.2.1]HEPTAN-2-ONE AND (-)-N-BOC-7-AZABICYCLO[2.2.1]HEPTAN-2-ONE VERSATILE INTERMEDIATES FOR THE ENANTIOSPECIFIC SYNTHESIS OF (+)-EPIBATIDINE AND (-)-EPIBATIDINE AND ANALOGS())

(+)- and (-)-Epibatidine, nonopiate antinociceptive alkaloids, have be en prepared from (-)- and (+)-N-BOC-7-azabicyclo[2.2.1]heptan-2-one wh ich were produced by resolution of the racemic mixture of the correspo nding alcohols obtained in the previous racemic synthesis. In the pres ent work, we report the enantiospecific synthesis of(-)- and (+)-N-BOC -7-azabicyclo[2.2.1]heptan-2-one from L-glutamic acid and levulinic ac id. Also, this report describes the selective formation of rans-2,3-di substituted-7-azabicyclo[2.2.1]heptanes from N-benzyl-5-(1'-methoxycar bonyl-3'-oxobutyl)proline via a decarbonylation/iminium ion cyclizatio n process. These functionalized intermediates are of potential value f or the enantiospecific synthesis of epibatidine analogues.