A new family of spermidine alkaloids typified by isocyclocelabenzine (1), 13-hydroxyisocyclocelabenzine (2), and cyclocelabenzine (3) were isolated from Maytenus mossmbicensis by Wagner and his co-workers.1 All three of these alkaloids each show the 13-membered lactam ring of celabenzine being linked to the benzoyl residue within the spermidine unit. These compounds have yet to be synthesized. We recently synthesized (±)-celabenzine and (–)-dihydrocelacinnine by the intramolecular reductive animation of an aldehyde to bring about the closure of the macrocyclic ring.2 The present paper describes a total synthesis of isocyclocelabenzine in which the macrocyclic ring is formed by the successive intramolecular reductive amination of aldehyde. © 1986, American Chemical Society. All rights reserved.