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The first synthesis of the title alkaloid (1) (+/- 3-β-benzoyloxy-8methyl-8-azabicyclo[3.2.1]octan-1-ol) is described from cyclohepta-3,5-dienol. The approach is extended to novel variants including the unknown noranalogue (3) and a derivative of the 6,7-dehydro-system. Detailed NMR data are presented. VT NMR studies show that (1) is effectively bicyclic, although there is evidence confirming the...
Synthetic approaches are described leading to homoepibatidine and bis-homoepibatidine which are based, respectively, on the tropane (8-azabicyclo[3.2.1]octane) and homotropane (9-azabicyclo-[4.2.1]nonane) ring systems. Epoxy- tropanes and -homotropanes (which are readily available from simple cyclic dienes) are convenient precursors for the azabicyclic alkenes needed for the key reductive coupling...
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