aluminium trichloride in benzene Ambient temperature;

1: 99 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature 2: 96 percent / MnO2 / CH2Cl2 / 6 h / Ambient temperature 3: 79 percent / triethylamine, NaBH3CN / ethanol / 14 h / Ambient temperature 4: 99 percent / ethyl formate / 20 h / Ambient temperature 5: 94 percent / methanesulfonic acid / 1 h / 70 °C / other reagent: polyphosphoric acid 6: 75 percent / p-toluenesulfonic acid monohydrate, chloranil / benzene / 15 h / Ambient temperature; other reagent: benzoquinone 7: 98 percent / m-chloroperbenzoic acid / CH2Cl2 / 4 h / Ambient temperature 8: 62 percent / triethylamine / acetonitrile / 3 h / Heating 9: 2.) HCl / 1.) THF, hexane, -50 deg C, 25 min, 2.) methanol, reflux, 5 min 10: 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: 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: 75 percent / p-toluenesulfonic acid monohydrate, chloranil / benzene / 15 h / Ambient temperature; other reagent: benzoquinone 2: 98 percent / m-chloroperbenzoic acid / CH2Cl2 / 4 h / Ambient temperature 3: 62 percent / triethylamine / acetonitrile / 3 h / Heating 4: 2.) HCl / 1.) THF, hexane, -50 deg C, 25 min, 2.) methanol, reflux, 5 min 5: 85 percent / AlCl3 / benzene / 2 h / Ambient temperature View Scheme

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

2: 98 percent / m-chloroperbenzoic acid / CH2Cl2 / 4 h / Ambient temperature 3: 62 percent / triethylamine / acetonitrile / 3 h / Heating 4: 2.) HCl / 1.) THF, hexane, -50 deg C, 25 min, 2.) methanol, reflux, 5 min 5: 85 percent / AlCl3 / benzene / 2 h / Ambient temperature View Scheme

1: 98 percent / m-chloroperbenzoic acid / CH2Cl2 / 4 h / Ambient temperature 2: 62 percent / triethylamine / acetonitrile / 3 h / Heating 3: 2.) HCl / 1.) THF, hexane, -50 deg C, 25 min, 2.) methanol, reflux, 5 min 4: 85 percent / AlCl3 / benzene / 2 h / Ambient temperature View Scheme

1: 62 percent / triethylamine / acetonitrile / 3 h / Heating 2: 2.) HCl / 1.) THF, hexane, -50 deg C, 25 min, 2.) methanol, reflux, 5 min 3: 85 percent / AlCl3 / benzene / 2 h / Ambient temperature View Scheme

1: 2.) HCl / 1.) THF, hexane, -50 deg C, 25 min, 2.) methanol, reflux, 5 min 2: 85 percent / AlCl3 / benzene / 2 h / Ambient temperature View Scheme

1: 80 percent / triethylamine, NaBH3CN / ethanol / 14 h / Ambient temperature 2: 99 percent / ethyl formate / 12 h / Ambient temperature 3: 75 percent / methanesulfonic acid / 3.5 h / 70 °C / other reagent: polyphosphoric acid 4: 72 percent / p-toluenesulfonic acid monohydrate, chloranil / benzene / 12 h / Ambient temperature; other reactant: 9-benzyl-2-formyl-4-oxo-1,2,3,4-tetrahydro-β-carboline, other reagent: benzoquinone, other reaction time 5: 74 percent / m-chloroperbenzoic acid / CH2Cl2 / 24 h / Ambient temperature 6: 61 percent / triethylamine / acetonitrile / 5 h / 70 °C 7: 97 percent / KOH / acetonitrile; H2O / 14 h / Ambient temperature 8: 2.) SiO2 / 1.) THF, hexane, -50 deg C, 30 min, 2.) 1 week; other reagent: H(1+) View Scheme