Enantioselective Total Syntheses of (+)-Kasugamycin and (+)-Kasuganobiosamine Highlighting a Sulfamate-Tethered Aza-Wacker Cyclization Strategy

Here, we present the first enantioselective total syntheses of the natural products (+)-kasugamycin, a potent antifungal antibiotic, and (+)-kasuganobiosamine, a compound that results from kasugamycin degradation. Salient features of these syntheses include a second-generation enantioselective preparation of a kasugamine derivative (much improved in efficiency relative to our first chiral-pool effort) and our laboratory’s sulfamate-tethered aza-Wacker cyclization.