[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1CC=C.C[N+]1([O-])CC[O:19]CC1.[CH3:23][C:24]([CH3:26])=[O:25]>O.O=[Os](=O)(=O)=O>[OH:25][CH:24]([CH2:26][OH:19])[CH2:23][C:3]1[C:2]([CH3:1])=[C:10]2[C:6](=[CH:5][CH:4]=1)[C:7](=[O:11])[O:8][CH2:9]2To a solution of 4-methyl-5-prop-2-en-1-yl-2-benzofuran-1(3H)-one (see step A for 1-3), (2.00 g, 10.6 mmol) in acetone (30 mL) and water (10 mL) was added OsO4 (0.27 g, 1.06 mmol) and NMO (6.70 g, 11.7 mmol), the solution was stirred at 25° C. for 18 h. The reaction mixture was diluted with water (30 mL) and the aqueous layer was extracted with CH2Cl2 (3×40 mL). The organic layers were combined, washed with brine (2×40 mL), dried with MgSO4, filtered and concentrated. The residue was purified by flash column chromatography (0-10% methanol in dichloromethane) to give the title compound.
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