[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[O:11])[CH2:8]2.C([O-])([O-])=[O:13].C([O-])([O-])=O.OO.OO.OO.[Na+].[Na+].[Na+].[Na+].C([O-])(O[O-])=O.[Na+].[Na+].O>C(O)(C(F)(F)F)=O>[CH2:6]1[C@@H:5]2[CH2:10][CH:1]3[O:13][C:2](=[O:11])[CH:3]([CH2:4]2)[CH2:9][C@@H:7]1[CH2:8]3Commercially available 2-adamantanone (×1) (1000 g, 6.66 mol, Sigma-Aldrich) was dissolved in TFA (3 L, Sigma-Aldrich). To this mechanically stirred mixture surrounded by a cooling bath with a temperature maintained at 20° C. was added sodium percarbonate (1254.8 g, 7.99 mol, Sigma-Aldrich) (or sodium peroxocarbonate) portion-wise over 1 h; the temperature of the reaction mixture increased to 60° C. during the addition. After 2 h additional stirring, deionized water (4 L) was added followed by four extractions with DCM (2 L for each extraction). The organic portions were combined, dried (MgSO4), filtered, and evaporated under reduced pressure to provide 1180 g of (1R,3r,6s,8S)-4-oxatricyclo[4.3.1.13,8]undecan-5-one (×2) as a white crystalline solid (yield 97%).
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