[I:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]1[CH2:12][CH:7]2C=C1.C[N+]1([O-])[CH2:19][CH2:18][O:17]CC1.[O-:21][Si]([O-])=O.[Mg+2].OS([O-])=O.[Na+]>CC(C)=O.O.O=[Os](=O)(=O)=O>[I:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]1[CH2:12][CH:7]2[CH:19]([OH:21])[CH:18]1[OH:17]5-Iodo-1,4-dihydro-1,4-methano-naphthalene (20 g) and N-methyl morpholine N-oxide (17.61 g, 130 mmol) were stirred in acetone (90 mL) and H2O (13 mL). To this was added a solution of OsO4 (0.2 mL, 2.5% wt, solution in t-BuOH, 0.02 mmol). After 144 hours, florisil (5 g) and saturated aqueous NaHSO3 solution (3 mL) were added and stirred for ½ hour. The mixture was filtered through a Celite pad and the filtrate concentrated to produce an oil which was purified by chromatography on Silica gel eluting with a gradient of hexanes to 100% EtOAc to provide a yellow solid (13.73 g). APCl MS m/e 301.1 [(M−1)+].
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