In summary, we developed a versatile synthetic entry to the cylindricine family of marine tricyclic alkaloids from a single common intermediate. We also revealed non-identity of the proposed structures of cylindricines I and J to the corresponding natural products. The asymmetric total synthesis of cylindricines A, B, F, G and the proposed structures of cylindricines I and J was achieved for the first time. Our synthesis took advantage of an appropriately functionalized spirocyclic pyrrolidine intermediate and completed in 10-15 steps from commercially available, oct-7-en-1-ol. A tandem chemoselective oxidation/intramolecular aza-Michael addition/epimerization was successfully implemented to complete the tricyclic skeleton of cylindricines in a succinct fashion.