A total synthesis of (+)-aspidospermidine (1) is described. The key reactions used in the synthesisof this pentacyclic Aspidosperma alkaloid were a deracemizing imine alkylation/Robinson annulationsequence, a selective “redox ketalization”, and an intramolecular Schmidt reaction. A Fischerindolization step carried out on a tricyclic ketone mirrored the sequence reported by Stork andDolfini in their classic aspidospermine synthesis.