1: 93 percent / tetrahydrofuran / 0.5 h / -10 °C 2: 69 percent / manganese dioxide / CH2Cl2 / 24 h / Ambient temperature 3: 64 percent / N-bromosuccinimide / benzene / 1 h / Irradiation 4: 55 percent / tris(trimethylsilyl)silane, azoisobutyronitrile (AIBN) / toluene / 2 h / 85 °C 5: 36 percent / boron tribromide / CH2Cl2 / 1 h / -40 °C View Scheme

1: 64 percent / N-bromosuccinimide / benzene / 1 h / Irradiation 2: 55 percent / tris(trimethylsilyl)silane, azoisobutyronitrile (AIBN) / toluene / 2 h / 85 °C 3: 36 percent / boron tribromide / CH2Cl2 / 1 h / -40 °C View Scheme

1: 1. potassium bis(trimethylsilylamide) / 1. THF, toluene, -78 deg C, 30 min; 2. -78 deg C, 45 min 2: sodium periodate / H2O; methanol / 12 h / Ambient temperature 3: toluene / 2 h / Heating 4: 87 percent / 20percent aq. NaOH / dimethylsulfoxide / 3 h / 120 °C 5: oxalyl chloride, DMF / tetrahydrofuran / 2 h / Ambient temperature 6: pyridine / CH2Cl2 / 24 h / Ambient temperature 7: 54 percent / mercuric chloride, mercuric oxide / acetonitrile; H2O / 1 h / Heating 8: 93 percent / tetrahydrofuran / 0.5 h / -10 °C 9: 69 percent / manganese dioxide / CH2Cl2 / 24 h / Ambient temperature 10: 64 percent / N-bromosuccinimide / benzene / 1 h / Irradiation 11: 55 percent / tris(trimethylsilyl)silane, azoisobutyronitrile (AIBN) / toluene / 2 h / 85 °C 12: 36 percent / boron tribromide / CH2Cl2 / 1 h / -40 °C View Scheme

1: 69 percent / manganese dioxide / CH2Cl2 / 24 h / Ambient temperature 2: 64 percent / N-bromosuccinimide / benzene / 1 h / Irradiation 3: 55 percent / tris(trimethylsilyl)silane, azoisobutyronitrile (AIBN) / toluene / 2 h / 85 °C 4: 36 percent / boron tribromide / CH2Cl2 / 1 h / -40 °C View Scheme

1: 55 percent / tris(trimethylsilyl)silane, azoisobutyronitrile (AIBN) / toluene / 2 h / 85 °C 2: 36 percent / boron tribromide / CH2Cl2 / 1 h / -40 °C View Scheme

1: 54 percent / mercuric chloride, mercuric oxide / acetonitrile; H2O / 1 h / Heating 2: 93 percent / tetrahydrofuran / 0.5 h / -10 °C 3: 69 percent / manganese dioxide / CH2Cl2 / 24 h / Ambient temperature 4: 64 percent / N-bromosuccinimide / benzene / 1 h / Irradiation 5: 55 percent / tris(trimethylsilyl)silane, azoisobutyronitrile (AIBN) / toluene / 2 h / 85 °C 6: 36 percent / boron tribromide / CH2Cl2 / 1 h / -40 °C View Scheme

1: sodium periodate / H2O; methanol / 12 h / Ambient temperature 2: toluene / 2 h / Heating 3: 87 percent / 20percent aq. NaOH / dimethylsulfoxide / 3 h / 120 °C 4: oxalyl chloride, DMF / tetrahydrofuran / 2 h / Ambient temperature 5: pyridine / CH2Cl2 / 24 h / Ambient temperature 6: 54 percent / mercuric chloride, mercuric oxide / acetonitrile; H2O / 1 h / Heating 7: 93 percent / tetrahydrofuran / 0.5 h / -10 °C 8: 69 percent / manganese dioxide / CH2Cl2 / 24 h / Ambient temperature 9: 64 percent / N-bromosuccinimide / benzene / 1 h / Irradiation 10: 55 percent / tris(trimethylsilyl)silane, azoisobutyronitrile (AIBN) / toluene / 2 h / 85 °C 11: 36 percent / boron tribromide / CH2Cl2 / 1 h / -40 °C View Scheme

1.1: magnesium / tetrahydrofuran / 0.5 h / 20 - 25 °C / Inert atmosphere 1.2: 1 h / Inert atmosphere 2.1: pyridinium p-toluenesulfonate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere 4.1: triphenylphosphine; diethylazodicarboxylate / diethyl ether; benzene / 14 h / 20 °C 5.1: pyridinium p-toluenesulfonate / ethanol / 1 h / 60 °C 6.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / toluene / 23 h / 80 °C / Inert atmosphere 7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 0.5 h / 20 °C / Inert atmosphere 8.1: aluminium(III) iodide; tetra-(n-butyl)ammonium iodide / benzene / 10 °C View Scheme

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere 2.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 4 h / 0 - 25 °C / Inert atmosphere 3.1: pyridinium p-toluenesulfonate / ethanol / 1 h / 60 °C 4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 0.5 h / 20 °C / Inert atmosphere 5.1: magnesium / tetrahydrofuran / 0.5 h / 20 - 25 °C / Inert atmosphere 5.2: 1 h / Inert atmosphere 6.1: pyridinium p-toluenesulfonate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere 8.1: triphenylphosphine; diethylazodicarboxylate / diethyl ether; benzene / 14 h / 20 °C 9.1: pyridinium p-toluenesulfonate / ethanol / 1 h / 60 °C 10.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / toluene / 23 h / 80 °C / Inert atmosphere 11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 0.5 h / 20 °C / Inert atmosphere 12.1: aluminium(III) iodide; tetra-(n-butyl)ammonium iodide / benzene / 10 °C View Scheme

1.1: pyridinium p-toluenesulfonate / dichloromethane / 0.5 h / 25 °C / Inert atmosphere 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 3.1: (R,R)-Co-salen; acetic acid / water; toluene / 20 °C / Cooling with ice 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere 5.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 4 h / 0 - 25 °C / Inert atmosphere 6.1: pyridinium p-toluenesulfonate / ethanol / 1 h / 60 °C 7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 0.5 h / 20 °C / Inert atmosphere 8.1: magnesium / tetrahydrofuran / 0.5 h / 20 - 25 °C / Inert atmosphere 8.2: 1 h / Inert atmosphere 9.1: pyridinium p-toluenesulfonate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere 11.1: triphenylphosphine; diethylazodicarboxylate / diethyl ether; benzene / 14 h / 20 °C 12.1: pyridinium p-toluenesulfonate / ethanol / 1 h / 60 °C 13.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / toluene / 23 h / 80 °C / Inert atmosphere 14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 0.5 h / 20 °C / Inert atmosphere 15.1: aluminium(III) iodide; tetra-(n-butyl)ammonium iodide / benzene / 10 °C View Scheme