1.1: pyridine / dichloromethane / 12 h / 20 °C / Inert atmosphere; Cooling with ice 2.1: bis-triphenylphosphine-palladium(II) chloride; 1,1'-bis-(diphenylphosphino)ferrocene; lithium chloride / N,N-dimethyl-formamide / 2 h / 180 °C / Inert atmosphere 2.2: 2 h / 20 °C 3.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / dichloromethane / 1 h / 50 °C / Inert atmosphere 4.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 4.2: 1 h / 50 °C 5.1: pyridinium chlorochromate / 1.5 h / 20 °C / Inert atmosphere 6.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 6.2: 4 h / -78 - 20 °C / Inert atmosphere 7.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C 8.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 9.1: sodium acetate / ethanol / 1 h / 80 °C 10.1: 1,2-dichloro-benzene / 1 h / Inert atmosphere; Heating; Microwave irradiation 11.1: palladium 10 on activated carbon / 1,2-dichloro-benzene / 180 °C 12.1: 12 h / 20 °C 12.2: 0.5 h / 20 °C 13.1: Jone's reagent / acetone / 0.5 h / 0 °C 13.2: Cooling with ice View Scheme

1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 2.1: sodium acetate / ethanol / 1 h / 80 °C 3.1: 1,2-dichloro-benzene / 1 h / Inert atmosphere; Heating; Microwave irradiation 4.1: palladium 10 on activated carbon / 1,2-dichloro-benzene / 180 °C 5.1: 12 h / 20 °C 5.2: 0.5 h / 20 °C 6.1: Jone's reagent / acetone / 0.5 h / 0 °C 6.2: Cooling with ice View Scheme

1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 4 h / -78 - 20 °C / Inert atmosphere 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 4.1: sodium acetate / ethanol / 1 h / 80 °C 5.1: 1,2-dichloro-benzene / 1 h / Inert atmosphere; Heating; Microwave irradiation 6.1: palladium 10 on activated carbon / 1,2-dichloro-benzene / 180 °C 7.1: 12 h / 20 °C 7.2: 0.5 h / 20 °C 8.1: Jone's reagent / acetone / 0.5 h / 0 °C 8.2: Cooling with ice View Scheme

1.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 1.2: 1 h / 50 °C 2.1: pyridinium chlorochromate / 1.5 h / 20 °C / Inert atmosphere 3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 3.2: 4 h / -78 - 20 °C / Inert atmosphere 4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 6.1: sodium acetate / ethanol / 1 h / 80 °C 7.1: 1,2-dichloro-benzene / 1 h / Inert atmosphere; Heating; Microwave irradiation 8.1: palladium 10 on activated carbon / 1,2-dichloro-benzene / 180 °C 9.1: 12 h / 20 °C 9.2: 0.5 h / 20 °C 10.1: Jone's reagent / acetone / 0.5 h / 0 °C 10.2: Cooling with ice View Scheme

1: 94 percent / 10percent NaOH / ethanol / Ambient temperature 2: 87 percent / acetic acid / 2-ethoxy-ethanol; H2O / 0.08 h / 110 - 120 °C 3: 91 percent / NaOH / H2O; ethanol / 4 h / Heating 4: 94 percent / H2, 1percent aq.PdCl2, Norit / acetic acid / 760 Torr / Ambient temperature 5: 86 percent / POCl3, K2CO3 / acetonitrile / 2.5 h / 55 - 60 °C 6: 1.) TiCl4, 2.) NaBH4 / 1.) CHCl3, a) RT, 2.5 h, b) reflux, 30 min, 2.) MeOH, RT, overnight 7: 91 percent / CHCl3 / 3 h / Heating 8: 89 percent / DDQ / benzene / 2 h / Heating 9: 77 percent / OsO4, pyridine / 2 h / Ambient temperature 10: 70 percent / HIO4*2H2O / H2O; dioxane / 2 h / Ambient temperature 11: 92 percent / K2CO3 / dimethylformamide / 2 h / Ambient temperature 12: 49 percent / 1.) p-toluenesulfonic acid, 2.) aq. 10percent HCl / xylene / 7.5 h / Heating View Scheme

1: 94 percent / 10percent NaOH / ethanol / Ambient temperature 2: 87 percent / acetic acid / 2-ethoxy-ethanol; H2O / 0.08 h / 110 - 120 °C 3: 91 percent / NaOH / H2O; ethanol / 4 h / Heating 4: 94 percent / H2, 1percent aq.PdCl2, Norit / acetic acid / 760 Torr / Ambient temperature 5: 86 percent / POCl3, K2CO3 / acetonitrile / 2.5 h / 55 - 60 °C 6: 1.) TiCl4, 2.) NaBH4 / 1.) CHCl3, a) RT, 2.5 h, b) reflux, 30 min, 2.) MeOH, RT, overnight 7: 91 percent / CHCl3 / 3 h / Heating 8: 89 percent / DDQ / benzene / 2 h / Heating 9: 77 percent / OsO4, pyridine / 2 h / Ambient temperature 10: 70 percent / HIO4*2H2O / H2O; dioxane / 2 h / Ambient temperature 11: 92 percent / K2CO3 / dimethylformamide / 2 h / Ambient temperature 12: 49 percent / 1.) p-toluenesulfonic acid, 2.) aq. 10percent HCl / xylene / 7.5 h / Heating View Scheme

1: 70 percent / CsF, N,N-diethylaniline / 3 h / Heating 2: 94 percent / 10percent NaOH / ethanol / Ambient temperature 3: 87 percent / acetic acid / 2-ethoxy-ethanol; H2O / 0.08 h / 110 - 120 °C 4: 91 percent / NaOH / H2O; ethanol / 4 h / Heating 5: 94 percent / H2, 1percent aq.PdCl2, Norit / acetic acid / 760 Torr / Ambient temperature 6: 86 percent / POCl3, K2CO3 / acetonitrile / 2.5 h / 55 - 60 °C 7: 1.) TiCl4, 2.) NaBH4 / 1.) CHCl3, a) RT, 2.5 h, b) reflux, 30 min, 2.) MeOH, RT, overnight 8: 91 percent / CHCl3 / 3 h / Heating 9: 89 percent / DDQ / benzene / 2 h / Heating 10: 77 percent / OsO4, pyridine / 2 h / Ambient temperature 11: 70 percent / HIO4*2H2O / H2O; dioxane / 2 h / Ambient temperature 12: 92 percent / K2CO3 / dimethylformamide / 2 h / Ambient temperature 13: 49 percent / 1.) p-toluenesulfonic acid, 2.) aq. 10percent HCl / xylene / 7.5 h / Heating 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 View Scheme

1: 92 percent / K2CO3 / dimethylformamide / 2 h / Ambient temperature 2: 49 percent / 1.) p-toluenesulfonic acid, 2.) aq. 10percent HCl / xylene / 7.5 h / Heating View Scheme

1: 58.3 percent / CsF, N,N-diethylaniline / 26.5 h / 215 °C 2: 77 percent / OsO4, pyridine / 2 h / Ambient temperature 3: 70 percent / HIO4*2H2O / H2O; dioxane / 2 h / Ambient temperature 4: 92 percent / K2CO3 / dimethylformamide / 2 h / Ambient temperature 5: 49 percent / 1.) p-toluenesulfonic acid, 2.) aq. 10percent HCl / xylene / 7.5 h / Heating View Scheme