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

1: 91 percent / NaOH / H2O; ethanol / 4 h / Heating 2: 94 percent / H2, 1percent aq.PdCl2, Norit / acetic acid / 760 Torr / Ambient temperature 3: 86 percent / POCl3, K2CO3 / acetonitrile / 2.5 h / 55 - 60 °C 4: 1.) TiCl4, 2.) NaBH4 / 1.) CHCl3, a) RT, 2.5 h, b) reflux, 30 min, 2.) MeOH, RT, overnight 5: 91 percent / CHCl3 / 3 h / Heating 6: 89 percent / DDQ / benzene / 2 h / Heating 7: 77 percent / OsO4, pyridine / 2 h / Ambient temperature 8: 70 percent / HIO4*2H2O / H2O; dioxane / 2 h / Ambient temperature 9: 92 percent / K2CO3 / dimethylformamide / 2 h / Ambient temperature 10: 49 percent / 1.) p-toluenesulfonic acid, 2.) aq. 10percent HCl / xylene / 7.5 h / Heating View Scheme

1: 86 percent / POCl3, K2CO3 / acetonitrile / 2.5 h / 55 - 60 °C 2: 1.) TiCl4, 2.) NaBH4 / 1.) CHCl3, a) RT, 2.5 h, b) reflux, 30 min, 2.) MeOH, RT, overnight 3: 91 percent / CHCl3 / 3 h / Heating 4: 89 percent / DDQ / benzene / 2 h / Heating 5: 77 percent / OsO4, pyridine / 2 h / Ambient temperature 6: 70 percent / HIO4*2H2O / H2O; dioxane / 2 h / Ambient temperature 7: 92 percent / K2CO3 / dimethylformamide / 2 h / Ambient temperature 8: 49 percent / 1.) p-toluenesulfonic acid, 2.) aq. 10percent HCl / xylene / 7.5 h / Heating View Scheme

1: 94 percent / H2, 1percent aq.PdCl2, Norit / acetic acid / 760 Torr / Ambient temperature 2: 86 percent / POCl3, K2CO3 / acetonitrile / 2.5 h / 55 - 60 °C 3: 1.) TiCl4, 2.) NaBH4 / 1.) CHCl3, a) RT, 2.5 h, b) reflux, 30 min, 2.) MeOH, RT, overnight 4: 91 percent / CHCl3 / 3 h / Heating 5: 89 percent / DDQ / benzene / 2 h / Heating 6: 77 percent / OsO4, pyridine / 2 h / Ambient temperature 7: 70 percent / HIO4*2H2O / H2O; dioxane / 2 h / Ambient temperature 8: 92 percent / K2CO3 / dimethylformamide / 2 h / Ambient temperature 9: 49 percent / 1.) p-toluenesulfonic acid, 2.) aq. 10percent HCl / xylene / 7.5 h / Heating View Scheme

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

1: With potassium hydroxide in water 2: With hydrogenchloride in water

xylene

CuCl; oxygen T=80°C; 10 h;

potassium hydroxide; potassium hexacyanoferrate(III)

CuCl; oxygen T=80°C; 10 h;