A modular approach has been developed for an efficient synthesis of an aminal group containing a new tetracyclic framework. The strategy has been devised based on selective hydrogen-bond-guided aza-Michael addition of heteroaromatic amines to cyclohexadienone-aldehydes. The reaction is highly atom economic and practical and involves stereoselective construction of four new C–N bonds and four rings. The synthetic utility of the tetracyclic product was explored. The role of a H-bond was explained with the help of experimental and density functional theory (DFT) computation studies.