1.1: potassium hydroxide / dimethyl sulfoxide / 0.5 h 1.2: 1 h 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C 3.1: manganese(IV) oxide / dichloromethane / 32 h / 20 °C View Scheme

1.1: manganese(IV) oxide / chloroform / 0 °C / |Reflux 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 2.2: 0.17 h / 0 °C View Scheme

1: 16.4 g / sodium hydride / hexamethylphosphoric acid triamide / 1.) 0 degC, 3 h, 2.) 0 degC to R.T., 2.5 h 2: 95 percent / hydrazine hydrate / ethanol / 3 h / Heating 3: 97 percent / pyridine / 1.) 0 degC, 0.5 h, 2.) 0 degC to R.T. 2 h 4: 1.6 g / potassium carbonate / ethane-1,2-diol / 150 °C View Scheme

1: 97 percent / pyridine / 1.) 0 degC, 0.5 h, 2.) 0 degC to R.T. 2 h 2: 1.6 g / potassium carbonate / ethane-1,2-diol / 150 °C View Scheme

1.1: potassium hydroxide / N,N-dimethyl-formamide / 0.33 h / 0 °C 1.2: 1 h / 0 - 20 °C 2.1: n-butyllithium / diethyl ether / 3 h / 20 °C / |Reflux 2.2: 3 h / |Reflux View Scheme

1: 79 percent / triethylamine, NaBH3CN / ethanol / 14 h / Ambient temperature 2: 99 percent / ethyl formate / 20 h / Ambient temperature 3: 94 percent / methanesulfonic acid / 1 h / 70 °C / other reagent: polyphosphoric acid 4: 75 percent / p-toluenesulfonic acid monohydrate, chloranil / benzene / 15 h / Ambient temperature; other reagent: benzoquinone 5: 65 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 1.) -50 deg C, 2 h, 2.) room temperature, 3 h 6: 74 percent / m-chloroperbenzoic acid / CH2Cl2 / 24 h / Ambient temperature View Scheme

1: 79 percent / triethylamine, NaBH3CN / ethanol / 14 h / Ambient temperature 2: 99 percent / ethyl formate / 20 h / Ambient temperature 3: 94 percent / methanesulfonic acid / 1 h / 70 °C / other reagent: polyphosphoric acid 4: 75 percent / p-toluenesulfonic acid monohydrate, chloranil / benzene / 15 h / Ambient temperature; other reagent: benzoquinone 5: 98 percent / m-chloroperbenzoic acid / CH2Cl2 / 4 h / Ambient temperature 6: 62 percent / triethylamine / acetonitrile / 3 h / Heating 7: 2.) HCl / 1.) THF, hexane, -50 deg C, 25 min, 2.) methanol, reflux, 5 min 8: 85 percent / AlCl3 / benzene / 2 h / Ambient temperature View Scheme

1: 79 percent / triethylamine, NaBH3CN / ethanol / 14 h / Ambient temperature 2: 99 percent / ethyl formate / 20 h / Ambient temperature 3: 94 percent / methanesulfonic acid / 1 h / 70 °C / other reagent: polyphosphoric acid 4: 75 percent / p-toluenesulfonic acid monohydrate, chloranil / benzene / 15 h / Ambient temperature; other reagent: benzoquinone 5: 65 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 1.) -50 deg C, 2 h, 2.) room temperature, 3 h 6: 74 percent / m-chloroperbenzoic acid / CH2Cl2 / 24 h / Ambient temperature 7: 61 percent / triethylamine / acetonitrile / 5 h / 70 °C 8: 97 percent / KOH / acetonitrile; H2O / 14 h / Ambient temperature 9: 90 percent / HCl / CH2Cl2 / 1.) room temperature, 24 h, 2.) reflux, 10 h View Scheme