The Nb-benzyl group (see 7) has been employed in the Pictet-Spengler reaction in refluxing benzene to provide complete retention of optical activity in this process. The tetrahydro-P-carbolines 3b (trans) and 4b (cis) were independently converted into the indolo substituted azabicyclo[3.3.1lnonane lb and its antipode lc, respectively. Consideration of the thermodynamic and kinetic parameters involved in both the Pictet-Spengler and Dieckmann condensations has now permitted the stereospecific synthesis of tetracyclic ketone 2 in high yield and in optically active form.