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: 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 View Scheme