1: 80 percent / NiCl2, NaBH4 / methanol / 0.33 h 2: 54 percent / Ac2O / 48 h / Ambient temperature 3: 82 percent / aq. NaOH / CH2Cl2; methanol / 1 h / Ambient temperature 4: 1.) NaH / 1.) THF, room temperature - 30 min, reflux - 15 min, 2.) THF, room temperature, 20 h 5: 100 percent / aq. NaOH / 24 h / Heating 6: ceric ammonium sulfate 7: NH3 View Scheme

1.1: sodium iodide / acetone / 5 h / |Inert atmosphere; |Reflux 2.1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; hexane / 0.67 h / -78 - 0 °C / |Inert atmosphere 2.2: 0.5 h / -78 - 0 °C / |Inert atmosphere 3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 0.33 h / 0 - 20 °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 / |Inert atmosphere 7.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C / |Inert atmosphere 8.1: ammonium chloride / ethanol / 0.33 h / |Inert atmosphere; |Reflux View Scheme

1.1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; hexane / 0.67 h / -78 - 0 °C / |Inert atmosphere 1.2: 0.5 h / -78 - 0 °C / |Inert atmosphere 2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 0.33 h / 0 - 20 °C / |Inert atmosphere 3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / |Inert atmosphere 4.1: water; sodium hydroxide / methanol / 0.5 h / |Reflux; |Inert atmosphere 5.1: Fremy’s salt / acetone / 0.33 h / 0 - 20 °C / pH 6.86 / |Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C / |Inert atmosphere 7.1: ammonium chloride / ethanol / 0.33 h / |Inert atmosphere; |Reflux View Scheme

1.1: acetonitrile / 4 h / |Reflux; |Inert atmosphere 2.1: AlCl3, aluminium chloride; lithium aluminium tetrahydride / diethyl ether / 0.33 h / 0 °C / |Inert atmosphere 3.1: triethylamine / 1,2-dichloro-ethane / 10 h / 20 °C / |Inert atmosphere 4.1: sodium iodide / acetone / 5 h / |Inert atmosphere; |Reflux 5.1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; hexane / 0.67 h / -78 - 0 °C / |Inert atmosphere 5.2: 0.5 h / -78 - 0 °C / |Inert atmosphere 6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 0.33 h / 0 - 20 °C / |Inert atmosphere 7.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / |Inert atmosphere 8.1: water; sodium hydroxide / methanol / 0.5 h / |Reflux; |Inert atmosphere 9.1: Fremy’s salt / acetone / 0.33 h / 0 - 20 °C / pH 6.86 / |Inert atmosphere 10.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C / |Inert atmosphere 11.1: ammonium chloride / ethanol / 0.33 h / |Inert atmosphere; |Reflux View Scheme

1: 99 percent / pyridine / 4 h / 60 °C 2: 1.) NaH 3: 95 percent / aq. NaOH 4: 77 percent / Fremy's salt 5: 41 percent / benzylamine hydrochloride, NaHCO3 / acetonitrile; methanol View Scheme

1: 77 percent / Fremy's salt 2: 41 percent / benzylamine hydrochloride, NaHCO3 / acetonitrile; methanol View Scheme

1: 1.) NaH 2: 95 percent / aq. NaOH 3: 77 percent / Fremy's salt 4: 41 percent / benzylamine hydrochloride, NaHCO3 / acetonitrile; methanol View Scheme

1: 95 percent / aq. NaOH 2: 77 percent / Fremy's salt 3: 41 percent / benzylamine hydrochloride, NaHCO3 / acetonitrile; methanol View Scheme

1: 1.) NaH / 1.) THF, room temperature - 30 min, reflux - 15 min, 2.) THF, room temperature, 20 h 2: 100 percent / aq. NaOH / 24 h / Heating 3: ceric ammonium sulfate 4: NH3 View Scheme

1: 100 percent / aq. NaOH / 24 h / Heating 2: ceric ammonium sulfate 3: NH3 View Scheme