A rare example of cyclization with 5-alkynones, which possess non-polar alkynyl and less electrophilic polar keto carbonyl groups, was demonstrated. The key to promoting carbene/alkyne metathesis followed by alkylidenation with pendant C[double bond, length as m-dash]O double bonds was the Schrock-type nucleophilic reactivity of the generated chromium carbene equivalents from readily available diiodomethanes and CrCl2 by simple heating.