In our retrosynthetic analysis (Figure ), we envisioned nucleophilic opening of activated oxathiazinane heterocycle B to set the C6 stereocenter of Bactobolin A. Tricyclic intermediate B would be synthesized by addition of CHCl2 -into ketone C followed by a Weinreb-inspired alkoxycarbonylation reaction. Ketone C would be prepared from sulfamate D using two sequential Wacker oxidations. The first would be our laboratory's sulfamate-tethered aza-Wacker cyclization reaction followed by a Tsuji-Wacker ketone synthesis. We planned to prepare sulfamate D using enone E, itself accessible from D-(-)-Quinic acid, a commercially available chiron.