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())
A. Hernandez et al., 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()), Journal of organic chemistry, 60(9), 1995, pp. 2683-2691
(+)- 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.