[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])C=2C=C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[N+]1([O-])CC[O:32]CC1.S([O-])([O-])=O.[Na+].[Na+].C1COCC1.[CH3:47][C:48]([CH3:50])=[O:49]>O.[Os](=O)(=O)(=O)=O>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:47]=2[CH:48]([OH:49])[CH2:50][OH:32])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1To a solution of methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-vinyl-1H-indole-6-carboxylate (from Step 2) in THF/acetone (0.2 M, 1:1, v:v) was added N-methyl morpholine N-oxide (1.2 eq.). To the resulting suspension water was added (1 volume part), followed by a solution of osmium tetroxide in water (0.1 eq., 4% solution). The resulting solution was left stirring overnight at RT. After one night a saturated solution of sodium sulfite in water was added and the mixture was left stirring for 30 min. The solution was diluted with water and extracted with DCM (3×) and EtOAc (2×). The combined organic extracts were dried over Na2SO4 and evaporated in vacuo. The residual material was dissolved in DCM and precipitated with PE. The product was obtained as a greyish foam (91%).
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