An asymmetric organocatalytic multi-component domino reaction is used as a key process for the stereoselective synthesis of polysubstituted mono-and bicyclic cyclohexene-carbaldehydes. Furthermore, the extension of the domino reaction and further synthetic transformations of the cascade products were investigated. The combination of the three-step cascade with an intramolecular DielsAlder reaction opens up an entry to tricyclic decahydroacenaphthylene and decahydrophenalene skeletons, which are valuable characteristic carbon cores of natural products.