Total synthesis of indole alkaloid (plusminus)-subincanadine F via Sm[I.sub.2]-medicated ring opening and bridge-forming Mannich reaction

The first total synthesis of (plusminus)-subincanadine F, a bioactive indole alkaloid structurally featuring a 1-azabicyclo[4.3.1]decane unit is obtained from 1-(para-methoxybenzyl)-tryptamine in six steps. The bridge-containing tetracyclic framework of subincanadine F was efficiently assembled by a Sm[I.sub.2]-mediated ring opening followed by an acid-mediated Mannich reaction.