1: 42 h / Ambient temperature 2: HCl(g) / acetonitrile / 20 h / -42 - 20 °C 3: 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / Ambient temperature 4: BF3*Et2O / benzene; methanol / 18 h / Ambient temperature 5: 50percent aq. AcOH / ethyl acetate / Ambient temperature 6: 87 percent / diphenylphosphoryl azide, 1,8-diazabicyclo<5.4.0>undec-7-ene / 23 h / Ambient temperature 7: 78 percent / H2S, pyridine / 1.5 h / Ambient temperature 8: diisopropylethylamine / dimethylformamide / 96 h / Ambient temperature 9: aq. NaOH / methanol / Ambient temperature View Scheme

1: BF3*Et2O / benzene; methanol / 18 h / Ambient temperature 2: 50percent aq. AcOH / ethyl acetate / Ambient temperature 3: 87 percent / diphenylphosphoryl azide, 1,8-diazabicyclo<5.4.0>undec-7-ene / 23 h / Ambient temperature 4: 78 percent / H2S, pyridine / 1.5 h / Ambient temperature 5: diisopropylethylamine / dimethylformamide / 96 h / Ambient temperature 6: aq. NaOH / methanol / Ambient temperature View Scheme

1: 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / Ambient temperature 2: BF3*Et2O / benzene; methanol / 18 h / Ambient temperature 3: 50percent aq. AcOH / ethyl acetate / Ambient temperature 4: 87 percent / diphenylphosphoryl azide, 1,8-diazabicyclo<5.4.0>undec-7-ene / 23 h / Ambient temperature 5: 78 percent / H2S, pyridine / 1.5 h / Ambient temperature 6: diisopropylethylamine / dimethylformamide / 96 h / Ambient temperature 7: aq. NaOH / methanol / Ambient temperature View Scheme

1: 87 percent / diphenylphosphoryl azide, 1,8-diazabicyclo<5.4.0>undec-7-ene / 23 h / Ambient temperature 2: 78 percent / H2S, pyridine / 1.5 h / Ambient temperature 3: diisopropylethylamine / dimethylformamide / 96 h / Ambient temperature 4: aq. NaOH / methanol / Ambient temperature View Scheme

1: HCl(g) / acetonitrile / 20 h / -42 - 20 °C 2: 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / Ambient temperature 3: BF3*Et2O / benzene; methanol / 18 h / Ambient temperature 4: 50percent aq. AcOH / ethyl acetate / Ambient temperature 5: 87 percent / diphenylphosphoryl azide, 1,8-diazabicyclo<5.4.0>undec-7-ene / 23 h / Ambient temperature 6: 78 percent / H2S, pyridine / 1.5 h / Ambient temperature 7: diisopropylethylamine / dimethylformamide / 96 h / Ambient temperature 8: aq. NaOH / methanol / Ambient temperature View Scheme

1.1: sodium methylate / methanol / 10 - 20 °C 2.1: sodium hydroxide; water / methanol / 15 - 25 °C 3.1: ammonium formate; ammonia / 25 - 90 °C 3.2: 1 h View Scheme

1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 2: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 3: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 4: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 5: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 6: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 7: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 8: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 9: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 10: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 11: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere 12: hydrogen / ethanol / 15 h / 20 °C / 760.05 Torr / Inert atmosphere 13: tetrahydrofuran / 29 h / 50 °C / Inert atmosphere 14: methanol; sodium methylate / 1 h / 20 °C / Inert atmosphere 15: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C / Inert atmosphere View Scheme

1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 3: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 4: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 5: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 6: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 7: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 8: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 9: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere 10: hydrogen / ethanol / 15 h / 20 °C / 760.05 Torr / Inert atmosphere 11: tetrahydrofuran / 29 h / 50 °C / Inert atmosphere 12: methanol; sodium methylate / 1 h / 20 °C / Inert atmosphere 13: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C / Inert atmosphere View Scheme

1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 2: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 3: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 4: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 5: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 6: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 7: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 8: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere 9: hydrogen / ethanol / 15 h / 20 °C / 760.05 Torr / Inert atmosphere 10: tetrahydrofuran / 29 h / 50 °C / Inert atmosphere 11: methanol; sodium methylate / 1 h / 20 °C / Inert atmosphere 12: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C / Inert atmosphere View Scheme

1: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 2: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere 3: hydrogen / ethanol / 15 h / 20 °C / 760.05 Torr / Inert atmosphere 4: tetrahydrofuran / 29 h / 50 °C / Inert atmosphere 5: methanol; sodium methylate / 1 h / 20 °C / Inert atmosphere 6: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C / Inert atmosphere View Scheme