MK-7655 (1) is a 尾-lactamase inhibitor in clinical trials as a combination therapy for the treatment of bacterial infection resistant to 尾-lactam antibiotics. Its unusual structural challenges have inspired a rapid synthesis featuring an iridium-catalyzed N鈥揌 insertion and a series of late stage transformations designed around the reactivity of the labile bicyclo[3.2.1]urea at the core of the target.