A convergent diastereoselective synthesis of racemic aristoserratine ((±)‐24) via an intramolecular iminium‐ion cyclization is described. The pivotal imine (±)‐19 was prepared by condensation of the two building blocks (± )‐trans‐8‐amino‐3‐(2,6‐difluorobenzyloxy)‐1‐p‐menthene ((±)‐11) and N‐(p‐methoxybenzenesulfonyl)‐3‐indo‐leacetaldehyde (18) which were synthesized from (±)‐trans‐1‐p‐menthene‐3,8‐diol ((±)‐7) and 3‐indoleacetic acid, respectively. On the route to the target (±)‐24, two previously unknown indole alkaloids have been characterized, namely (±)‐‘anti’‐hobartin‐15‐ol ((±)‐22) and (±)‐‘anti’‐aristotelin‐15‐ol ((±)‐23). Copyright © 1989 Verlag GmbH & Co. KGaA, Weinheim