Stereocontrolled reduction of an oxazepinohexahydroindolo[2,3-a]quinolizine derivative: asymmetric total synthesis of (+)-tacamonine

Efficient, stereocontrolled total synthesis of the title compound is described, starting from enantiopure intermediates. A key step was the diastereoselective catalytic hydrogenation of a pentacyclic oxazepinohexahydroindolo[2,3-a]quinolizine derivative.