1.1: NaH / dimethylformamide / -20 - 20 °C 2.1: 6.24 g / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 3.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 4.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 5.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 6.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 7.1: 73 percent / benzene / 48 h / 80 °C 8.1: 84 percent / benzene / 39 h / 70 °C 9.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 10.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 11.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 13.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 13.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 14.1: DMAP / pentane / 168 h / 20 °C 14.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 15.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 16.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 17.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 18.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 19.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 20.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 22.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 23.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 24.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 25.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 26.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme