AbstractAn enyne metathesis/ring closing metathesis (EM/RCM) sequence was used to synthesise acyloxy‐semicyclic dienes from an enyne substrate and various vinyl esters. This allowed convenient access to acyloxy‐semicyclic dienes not accessible by cross metathesis alone due to the low reactivity of Fischer carbenes with the termini of 1,3‐dienes. This new approach also provides an alternative method for the synthesis of 1‐acyloxy‐1,3‐dienes which are useful reactants for Diels–Alder cycloadditions.