1: in acetone T=60°C; 0.5 h; Sealed tubeInert atmosphere; 2: With potassium iodide in acetone T=70°C; 7 h; Sealed tubeInert atmosphere;

sodium hydroxide in methanol T=25°C; 0.5 h;

1: 96 percent / H2O / 3 h / 25 °C 2: 96 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 4 h / Heating 3: 90 percent / NaOH / CTAB / CH2Cl2 / 12 h / 25 °C 4: 76 percent / acetonitrile / 0.5 h / 0 °C 5: 71 percent / BBr3 / CH2Cl2 / 12 h / 0 - 25 °C 6: 86 percent / CAN / acetonitrile / 0.17 h / 0 °C 7: 36 percent / dithienyl ditelluride, NaBH4, NaOH / tetrahydrofuran; H2O / 6 h / 67 °C 8: 76 percent / 10percent NaOH / methanol / 0.5 h / 25 °C View Scheme

1: 90 percent / NaOH / CTAB / CH2Cl2 / 12 h / 25 °C 2: 76 percent / acetonitrile / 0.5 h / 0 °C 3: 71 percent / BBr3 / CH2Cl2 / 12 h / 0 - 25 °C 4: 86 percent / CAN / acetonitrile / 0.17 h / 0 °C 5: 36 percent / dithienyl ditelluride, NaBH4, NaOH / tetrahydrofuran; H2O / 6 h / 67 °C 6: 76 percent / 10percent NaOH / methanol / 0.5 h / 25 °C View Scheme

1: 96 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 4 h / Heating 2: 90 percent / NaOH / CTAB / CH2Cl2 / 12 h / 25 °C 3: 76 percent / acetonitrile / 0.5 h / 0 °C 4: 71 percent / BBr3 / CH2Cl2 / 12 h / 0 - 25 °C 5: 86 percent / CAN / acetonitrile / 0.17 h / 0 °C 6: 36 percent / dithienyl ditelluride, NaBH4, NaOH / tetrahydrofuran; H2O / 6 h / 67 °C 7: 76 percent / 10percent NaOH / methanol / 0.5 h / 25 °C View Scheme

1: 51 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 2: H2 / 10percent Pd-BaSO4 / methanol / 1.5 h / Ambient temperature 3: air, Et3N / methanol / 1 h / Ambient temperature View Scheme

1: 63 percent / HNO3 / 1.) -50-(-40) deg C, 1 h, 2.) -30 deg C, 25 min 2: 73 percent / TFA, t-BuI, I2, FeCl2 / dimethylsulfoxide / 5 h / 80 - 85 °C 3: 93 percent / HCl / diethyl ether / 65 h / Heating 4: 4 Angstroem sieves / CH2Cl2 / 22 h / Ambient temperature 5: NiCl2, NaBH4 / methanol / 0.08 h 6: 14 percent / Bu4NHSO4, NaOH / CH2Cl2 / 3 h / Ambient temperature 7: 37 percent / 4 Angstroem sieves, BBr3 / CH2Cl2 / 1.) -78 deg C - (-30) deg C, 1.5 h, 2.) -30 deg C - (-20) deg C, 30 min 8: aq. NaOH View Scheme

1: 73 percent / TFA, t-BuI, I2, FeCl2 / dimethylsulfoxide / 5 h / 80 - 85 °C 2: 93 percent / HCl / diethyl ether / 65 h / Heating 3: 4 Angstroem sieves / CH2Cl2 / 22 h / Ambient temperature 4: NiCl2, NaBH4 / methanol / 0.08 h 5: 14 percent / Bu4NHSO4, NaOH / CH2Cl2 / 3 h / Ambient temperature 6: 37 percent / 4 Angstroem sieves, BBr3 / CH2Cl2 / 1.) -78 deg C - (-30) deg C, 1.5 h, 2.) -30 deg C - (-20) deg C, 30 min 7: aq. NaOH View Scheme

1: 1.) AcOH, FeCl3, 2.) AcOH / 1.) 60 deg C, 5 min, 2.) reflux, 5 h 2: 63 percent / HNO3 / 1.) -50-(-40) deg C, 1 h, 2.) -30 deg C, 25 min 3: 73 percent / TFA, t-BuI, I2, FeCl2 / dimethylsulfoxide / 5 h / 80 - 85 °C 4: 93 percent / HCl / diethyl ether / 65 h / Heating 5: 4 Angstroem sieves / CH2Cl2 / 22 h / Ambient temperature 6: NiCl2, NaBH4 / methanol / 0.08 h 7: 14 percent / Bu4NHSO4, NaOH / CH2Cl2 / 3 h / Ambient temperature 8: 37 percent / 4 Angstroem sieves, BBr3 / CH2Cl2 / 1.) -78 deg C - (-30) deg C, 1.5 h, 2.) -30 deg C - (-20) deg C, 30 min 9: aq. NaOH View Scheme

1.1: sodium iodide / acetone / 5 h / |Inert atmosphere; |Reflux 2.1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / |Inert atmosphere; |Schlenk technique 3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 0.33 h / 0 °C / |Inert atmosphere 4.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / |Inert atmosphere 5.1: water; sodium hydroxide / methanol / 0.5 h / |Reflux; |Inert atmosphere 6.1: Fremy’s salt / acetone / 0.33 h / 0 - 20 °C / pH 6.86 7.1: acetone / 0.5 h / 60 °C / |Sealed tube; |Inert atmosphere 7.2: 7 h / 70 °C / |Sealed tube; |Inert atmosphere View Scheme