Synthesis of physoperuvine (8-methyl-8-azabicyclo[3.2.1]octan-1-ol), norphysoperuvine and dehydro-derivates

Abstract

4-Aminocycloheptanones have been synthesised in high yield from cyclohepta-1,3-diene. These compounds exist mainly as the bicyclic tautomers (8-azabicyclo[3.2.1 ]octan-1-ol derivatives; the title compounds) as shown by ¹³C NMR spectroscopy at low temperatures. 4-Aminocyclohept-2enones are reactive but show a preference for the monocyclic tautomers; N-benzyloxycarbonyl derivatives of the saturated and unsaturated systems are isolated as the monocyclic tautomers.