Kaurane diterpenes (kaurenes) are highly abundant among the plant kingdom and are potentially useful as antibiotics, antimalarials, and antifeedants.  In this research we show how the net [5+5]-cycloaddition of a variety of enynones (i.e. 2-alkynylbenzophenone, 1) with exocyclic gamma,delta-unsaturated Fischer carbene complexes (2) achieves the sought after bridged hydrophenanthrene ring system (3) of kaurenes in a single step.  Coupling of the carbene with the enynone generates a very reactive isobenzofuran intermediate that can undergo an intramolecular Diels-Alder reaction with the alkene of the carbene complex to give the desired product.  In this study we explore the scope and limitations of both the enynones and the carbene complexes as well as investigate the synthetic challenges needed to complete the total synthesis of kaurene analogs.