We have developed a new strategy for the preparation ofdiolides using a cascade of Nicholas reactions. The carboxylicacid nucleophiles in these reactions are virtually unstudiedparticipants in transformations of this type. Using thismethodology, a 16-membered cobalt-complexed cyclic diyneis available in 28% yield over eight steps (an average of 85%per step). We can also easily access the uncomplexed diolidein one additional step.