1: pyridine / CH2Cl2 2: 85 percent / OsO4; 4-methylmorpholine N-oxide / tetrahydrofuran; H2O 3: 100 percent / pyridinium p-toluenesulfonate / toluene / Heating 4: K2CO3; MeOH 5: tetrabutylammonium perruthenate; 4-methylmorpholine N-oxide / CH2Cl2 6: 40 percent / methanol / 2 h / UV-irradiation 7: 90 percent / aq. CF3CO2H / 20 °C View Scheme

manganese(IV) oxide in dichloromethane T=20°C; 5 h;

1: bis(acetylacetonato) palladium / 10 °C 2: manganese(IV) oxide / dichloromethane / 20 °C 3: manganese(IV) oxide; sulfuric acid / water / 48 h / 20 °C 4: potassium permanganate; sulfuric acid / water View Scheme

1: 94 percent / n-Bu3P / tetrahydrofuran / 0.5 h / 20 °C 2: 89 percent / aq. H2O2; pyridine / 4 h / -20 - 20 °C View Scheme