Abstract Triazacryptand (TAC)-based fluorescent K+ sensors have broad biomedical utility, yet their advancement has been hindered because of their challenging synthesis. Herein, an efficient synthesis is reported that delivers a didesmethyl triazacryptand (ddTAC) K+ sensor in twofold fewer steps and ninefold higher overall yield than the original TAC synthesis. Our synthesis utilizes a C–O dianionic oxidative macrocyclization and reports new examples ...