[CH2:1]=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4][CH2:3]1.[OH2:17].C[N+]1([O-])CCOCC1.S([O-])([O-])=O.[Na+].[Na+].[OH2:32]>O1CCCC1.O.O.[O-][Os]([O-])(=O)=O.[K+].[K+]>[CH2:10]([O:9][CH2:8][CH:5]1[CH2:6][CH2:7][C:2]([CH2:1][OH:32])([OH:17])[CH2:3][CH2:4]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1
To a solution of EXAMPLE 399A (4.77 g) and 4-methylmorpholine 4-oxide hydrate (3.28 g), in a mixture of tetrahydrofuran (90 mL) and water (13.50 mL) was added potassium dioxidodioxoosmium dihydrate (0.325 g) and the resulting suspension was stirred rapidly 18 hours. Sodium sulfite (12.51 g) and water (90 mL) were added and stirring was continued for 1 hour. The reaction was diluted with water (300 mL) and extracted with ethyl acetate (3×200 mL). The combined organics were dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel and eluted with a 50, 100% ethyl acetate in hexane step gradient to provide the title compound.
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