[CH3:1][O:2][C:3]([C:5]1([CH2:10][CH2:11][CH:12]=C)[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].I([O-])(=O)(=O)=[O:15].[Na+]>C(O)(C)C.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3]([C:5]1([CH2:10][CH2:11][CH:12]=[O:15])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4]To a solution of 1-but-3-enyl-cyclopentanecarboxylic acid methyl ester (4.0 g, 21.5 mmol) in isopropanol (35 mL) was added a solution of sodium periodate (10.1 g, 47.3 mmol) in H2O (35 mL) followed by the addition of osmium tetroxide (16 mg, 0.065 mmol). More isopropanol (30 mL) and H2O (35 mL) were added and the resulting suspension was stirred for 24 hours and then poured onto ice/H2O (200 mL) and extracted with EtOAc (2×200 mL). The organic layers were combined and dried over Na2SO4, filtered and concentrated to provide a crude oil which was purified by flash column chromatography (10 to 60% EtOAc/heptane) to provide 2.27 g (57 yield over two steps) of the title compound as an oil.
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