[CH2:1]([C:4]1([OH:14])[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5]1)[CH:2]=C.C([O:17]CC)C.[O-]S([O-])(=S)=O.[Na+].[Na+]>O=[Os](=O)(=O)=O.O>[OH:14][C:4]1([CH2:1][CH:2]=[O:17])[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5]1NalO4 (18.13 g) followed by OsO4 (4% in water, 0.96 mL) is added to a mixture of 8-allyl-1,4-dioxa-spiro[4.5]decan-8-ol (12.59 g), diethyl ether (65 ml), and water (85 mL) at room temperature. The mixture is vigorously stirred at room temperature overnight, before aqueous Na2S2O3 solution (50 mL) is added and stirring is continued for another 45 min. The combined organic phases are washed with water, dried (MgSO4), and concentrated. The crude product is used without further purification. Yield: 2.68 g (ca. 70% pure); Mass spectrum (ESI+): m/z=201 [M+H]+.
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