A diversity-oriented approach for the synthesis of various structurally different molecular frameworks from readily accessible and common precursors is described. A Claisen rearrangement followed by ring-closing metathesis or ethylene-promoted ring-closing enyne metathesis has been utilized as the key synthetic transformation to generate naphthoxepine derivatives. The ring-closing metathesis approach has also been used to generate spirocyclic compounds and the pleiadene framework.