Exo- and Endo-6-Hydroxy- and 6,7-Epoxytropanes; Total Synthesis of Scopine, Pseudoscopine, and Nor- Derivatives

Article abstract of DOI:10.1016/0040-4039(95)00836-2

Novel endo- 6,7-epoxy-8-azabicyclo<3.2.1>octane derivatives and the corresponding exo-analogues have been synthesised and show substantially different reactivity; the resistance of the exo-epoxides to ring opening during hydride reduction and catalytic hydrogenolysis is exploited in a total synthesis of scopine, pseudoscopine, and nor- derivatives.