An efficient diverse synthesis of cis-fused indenopiperidines and bridged benzomorphanones, starting from cyclopropane-fused benzomorphanothiones and benzomorphanones, respectively, using NaBH4/NiCl2·6H2O/EtOH as a reducing system, is described. High rigidity of substrates allowed axially controlled syntheses of their trans-mono-alkylated derivatives, subsequently enabling access to both trans-alkyl-functionalized benzobicyclic piperidin(on)es. Diversity-oriented synthesis of naphthalene ring-containing fused naphthoindenopiperidines and bridged naphthomorphanone directly from 2-pyridones was also performed.