1: 87 percent / NaH / tetrahydrofuran / 24 h / 40 °C 2: 68 percent / aq. NaN3; NH4Cl / ethanol / 48 h / Heating 3: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C 4: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C 5: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C 6: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C 7: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C 8: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C 9: 65 percent / pyridine / 12 h / 20 °C 10: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C 11: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C View Scheme