1: 76.3 mg / palladium(II) acetylacetonate; tributylphosphine; ammonium formate / toluene / 1 h / 70 °C 2: 97 percent / DDQ / CH2Cl2; H2O / 0.5 h / 20 °C 3: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 4: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.6 Torr 5: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 6: 96 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / 20 °C 7: 89 percent / N-methylmorpholine N-oxide; tetrapropylammonium perruthenate; molecular sieves 4 Angstroem / CH2Cl2 / 0.5 h / 20 °C 8: 92 percent / samarium(II) iodide / tetrahydrofuran / 0.33 h / -78 °C 9: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 10: 347.4 mg / LiOH; H2O2 / tetrahydrofuran; H2O / 3 h / 0 °C 11: triethylamine / benzene / 1 h / 20 °C 12: 97 percent / 4-(dimethylamino)pyridine / benzene / 0.5 h / 20 °C 13: 93 percent / PPTS / ethanol / 10 h / 50 °C 14: 79 percent / N-methylmorpholine N-oxide; tetrapropylammonium perruthenate; molecular sieves 4 Angstroem / CH2Cl2 / 0.5 h / 20 °C 15: 19 percent / SmI2; HMPA / tetrahydrofuran / 0.5 h / -78 °C 16: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17: 8.5 mg / CeCl3*7H2O; NaBH4 / methanol / 0.17 h / 0 °C 18: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 19: 90 percent / DDQ / CH2Cl2; H2O / 0.25 h / 0 °C 20: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / H2O; 2-methyl-propan-2-ol / 0.5 h / 20 °C 22: 5.2 mg / HF*pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme