Birch reduction;

1.1: SOCl2 / pyridine 2.1: RuCl3; NaIO4 / acetonitrile; CCl4; H2O 3.1: DBU / acetonitrile / 0.5 h / 20 °C 3.2: acetonitrile / 2 h / 75 °C 3.3: silica gel / CH2Cl2; methanol 4.1: HCl / methanol; H2O / 20 h / 65 °C View Scheme

1.1: RuCl3; NaIO4 / acetonitrile; CCl4; H2O 2.1: DBU / acetonitrile / 0.5 h / 20 °C 2.2: acetonitrile / 2 h / 75 °C 2.3: silica gel / CH2Cl2; methanol 3.1: HCl / methanol; H2O / 20 h / 65 °C View Scheme

1: 75 percent / trimethylsilyl trifluoromethanesulfonate (TMSOTf), Et3SiH / CH2Cl2 / 18.5 h / Ambient temperature 2: 97 percent / DMAP, Et3N / CH2Cl2 / 2 h / Ambient temperature 3: 49.5 percent / K2CO3, 18-crown-6 / dimethylformamide / 20 h / 120 °C 4: 78 percent / BCl3 / hexane; CH2Cl2 / 1.) -78 deg C, 2.5 h; 2.) -18 deg C, 4 h View Scheme

1: pyridine / 0 °C 2: 1.04 g / SOCl2; pyridine / 20 °C 3: 78 percent / NaN3 / dimethylformamide / 3 h / 80 °C 4: 91 percent / H2 / Pd/C / ethanol / 6 h / 1292.87 Torr 5: 52 percent / pyridine / 1-methyl-pyrrolidin-2-one / 5 h / 140 °C 6: 90 percent / conc. HCl / 5 h / 20 °C 7: 82 percent / NH4F / methanol / Heating 8: NH3 / methanol View Scheme

1: 91 percent / H2 / Pd/C / ethanol / 6 h / 1292.87 Torr 2: 52 percent / pyridine / 1-methyl-pyrrolidin-2-one / 5 h / 140 °C 3: 90 percent / conc. HCl / 5 h / 20 °C 4: 82 percent / NH4F / methanol / Heating 5: NH3 / methanol View Scheme

1: NaH / dimethylformamide / 13.5 h / Ambient temperature 2: 75 percent / trimethylsilyl trifluoromethanesulfonate (TMSOTf), Et3SiH / CH2Cl2 / 18.5 h / Ambient temperature 3: 97 percent / DMAP, Et3N / CH2Cl2 / 2 h / Ambient temperature 4: 49.5 percent / K2CO3, 18-crown-6 / dimethylformamide / 20 h / 120 °C 5: 78 percent / BCl3 / hexane; CH2Cl2 / 1.) -78 deg C, 2.5 h; 2.) -18 deg C, 4 h View Scheme

1: NaIO4 / methanol; H2O / 0.5 h / Ambient temperature 2: NaBH4 / H2O; methanol / 0.5 h / Ambient temperature 3: NaH / dimethylformamide / 13.5 h / Ambient temperature 4: 75 percent / trimethylsilyl trifluoromethanesulfonate (TMSOTf), Et3SiH / CH2Cl2 / 18.5 h / Ambient temperature 5: 97 percent / DMAP, Et3N / CH2Cl2 / 2 h / Ambient temperature 6: 49.5 percent / K2CO3, 18-crown-6 / dimethylformamide / 20 h / 120 °C 7: 78 percent / BCl3 / hexane; CH2Cl2 / 1.) -78 deg C, 2.5 h; 2.) -18 deg C, 4 h View Scheme

1: 80percent AcOH / 9 h / Ambient temperature 2: NaIO4 / methanol; H2O / 0.5 h / Ambient temperature 3: NaBH4 / H2O; methanol / 0.5 h / Ambient temperature 4: NaH / dimethylformamide / 13.5 h / Ambient temperature 5: 75 percent / trimethylsilyl trifluoromethanesulfonate (TMSOTf), Et3SiH / CH2Cl2 / 18.5 h / Ambient temperature 6: 97 percent / DMAP, Et3N / CH2Cl2 / 2 h / Ambient temperature 7: 49.5 percent / K2CO3, 18-crown-6 / dimethylformamide / 20 h / 120 °C 8: 78 percent / BCl3 / hexane; CH2Cl2 / 1.) -78 deg C, 2.5 h; 2.) -18 deg C, 4 h View Scheme

1: trimethylsilyl trifluoromethanesulfonate (TMSOTf), Et3SiH / CH2Cl2 / Ambient temperature 2: 97 percent / DMAP, Et3N / CH2Cl2 / 2 h / Ambient temperature 3: 49.5 percent / K2CO3, 18-crown-6 / dimethylformamide / 20 h / 120 °C 4: 78 percent / BCl3 / hexane; CH2Cl2 / 1.) -78 deg C, 2.5 h; 2.) -18 deg C, 4 h View Scheme