1: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 2: 19 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 3: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 4: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 5: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 6: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 7: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 8: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 9: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme