1: 1.) TiCl4, 2.) NaBH4 / 1.) CHCl3, a) RT, 2.5 h, b) reflux, 30 min, 2.) MeOH, RT, overnight 2: 91 percent / CHCl3 / 3 h / Heating 3: 89 percent / DDQ / benzene / 2 h / Heating 4: 77 percent / OsO4, pyridine / 2 h / Ambient temperature 5: 70 percent / HIO4*2H2O / H2O; dioxane / 2 h / Ambient temperature 6: 92 percent / K2CO3 / dimethylformamide / 2 h / Ambient temperature 7: 49 percent / 1.) p-toluenesulfonic acid, 2.) aq. 10percent HCl / xylene / 7.5 h / Heating View Scheme

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

1: 1.) TiCl4, 2.) NaBH4 / 1.) CHCl3, a) RT, 2.5 h, b) reflux, 30 min, 2.) MeOH, RT, overnight 2: 91 percent / CHCl3 / 3 h / Heating 3: 89 percent / DDQ / benzene / 2 h / Heating 4: 77 percent / OsO4, pyridine / 2 h / Ambient temperature 5: 70 percent / HIO4*2H2O / H2O; dioxane / 2 h / Ambient temperature 6: 92 percent / K2CO3 / dimethylformamide / 2 h / Ambient temperature 7: 49 percent / 1.) p-toluenesulfonic acid, 2.) aq. 10percent HCl / xylene / 7.5 h / Heating 8: 76 percent / NaBH4 / methanol / 0.5 h / Ambient temperature View Scheme