Studies on the syntheses of heterocyclic compounds. Part 782. Another total synthesis of (±)-tubulosine and (±)-deoxytubulosine

(±)-Tubulosine (1) and (±)-deoxytubulosine (3) were totally synthesized by the Pictet–Spengler reaction of (±)-4-oxoprotoemetine (7) with serotonin (8) or tryptamine (9) followed by reduction with sodium bis(2-methoxyethoxy)aluminum hydride in pyridine.