A short total synthesis of the indolopyridine alkaloids angustine (1) and angustoline (2) has been achieved in five and six steps, respectively. Two key steps for assembly of the pentacyclic core included a Bischler-Napieralski cyclization and a cobalt-catalyzed carbonylative lactamization. A late-stage Mukaiyama hydration allowed the first successful transformation of angustine (1) to angustoline (2). © 2020