1: 77 percent / OsO4, pyridine / 2 h / Ambient temperature 2: 70 percent / HIO4*2H2O / H2O; dioxane / 2 h / Ambient temperature 3: 92 percent / K2CO3 / dimethylformamide / 2 h / Ambient temperature 4: 49 percent / 1.) p-toluenesulfonic acid, 2.) aq. 10percent HCl / xylene / 7.5 h / Heating View Scheme

2: 2.) p-toluenesulfonic acid / 1.) xylene, 2.) reflux View Scheme

1: 77 percent / OsO4, pyridine / 2 h / Ambient temperature 2: 70 percent / HIO4*2H2O / H2O; dioxane / 2 h / Ambient temperature 3: 92 percent / K2CO3 / dimethylformamide / 2 h / Ambient temperature 4: 49 percent / 1.) p-toluenesulfonic acid, 2.) aq. 10percent HCl / xylene / 7.5 h / Heating 5: 76 percent / NaBH4 / methanol / 0.5 h / Ambient temperature View Scheme