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

Abstract

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

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