A strategy featuring the application of contemporary methods for the selective oxidation of C–H and -bonds is outlined for the synthesis of pactamycin. Chemoselective oxidative cyclization of an intermediate sulfamate introduces the first of three N-centers. By employing this technology, the core of C2-epi-pactamycate has been successfully assembled. The many challenges associated with the synthesis of pactamycin and related aminocyclitol natural products will continue to drive innovation in oxidation catalysis.