AuI-catalyzed cyclizations of functionalized enynes lead to the ready assembly of tricyclic carbon skeletons that are present in a number of naturally occurring compounds. An alkenyl gold intermediate is formed in the cyclization of the enynes and can be trapped in 5-exo-dig or 6-endo-dig Prins reactions to form an additional CC bond. Z=C(CO₂Me)₂, NTs; R=H, Me, iPr