1: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 2: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 3: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 4: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 5: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 6: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

1: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 2: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 3: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 4: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 5: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 6: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 7: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

1: 1.) trifluoroacetic acid, 2.) K2CO3, MeOH / 1.) CH2Cl2, 23 deg C, 24 h, 2.) 23 deg C, 1 h 2: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C 3: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 4: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 5: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 6: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 7: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 8: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 9: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 10: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

1: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 2: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 3: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 4: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 5: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 6: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 7: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 8: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

1: 98 percent / BF3*Et2O / methanol / 2.5 h / 0 - 5 °C 2: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature 3: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C 4: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 5: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme

1: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature 2: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C 3: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 4: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme

1: 85 percent / SO3 pyridine complex / triethylamine; dimethylsulfoxide / 3 h / Ambient temperature 2: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C 3: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification 4: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature 5: 85 percent / Li, ethylenediamine / tetrahydrofuran / 2 h / 25 °C / continuous flow of ethyne View Scheme

1: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C 2: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification 3: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature 4: 85 percent / Li, ethylenediamine / tetrahydrofuran / 2 h / 25 °C / continuous flow of ethyne View Scheme

1: 92 percent / HCl / acetone; H2O 2: boron trifluoride diethyl ether / methanol / 1 h / Ambient temperature 3: 87 percent / Li, ethylamine / tetrahydrofuran / 0.5 h / -35 - -30 °C 4: 85 percent / SO3 pyridine complex / triethylamine; dimethylsulfoxide / 3 h / Ambient temperature 5: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C 6: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification 7: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature 8: 85 percent / Li, ethylenediamine / tetrahydrofuran / 2 h / 25 °C / continuous flow of ethyne View Scheme

1: 87 percent / Li, ethylamine / tetrahydrofuran / 0.5 h / -35 - -30 °C 2: 85 percent / SO3 pyridine complex / triethylamine; dimethylsulfoxide / 3 h / Ambient temperature 3: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C 4: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification 5: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature 6: 85 percent / Li, ethylenediamine / tetrahydrofuran / 2 h / 25 °C / continuous flow of ethyne View Scheme