1: 92 percent / p-TsOH / CH2Cl2 / 1.5 h / Ambient temperature 2: 67 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -78 °C 3: 83 percent / pyridine / Ambient temperature 4: 95 percent / p-TsOH, MeOH / 0.05 h / 50 °C 5: 77 percent / aluminium isopropoxide / toluene; cyclohexanone / 20 h / Heating 6: 28 percent / KMnO4, triethylbenzylammonium chloride (TEBACl) / CH2Cl2 / Ambient temperature View Scheme

1: 92 percent / p-TsOH / CH2Cl2 / 1.5 h / Ambient temperature 2: 67 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -78 °C 3: 83 percent / pyridine / Ambient temperature 4: 47 percent / KMnO4, triethylbenzylammonium chloride (TEBACl) / CH2Cl2 / Ambient temperature 5: p-TsOH, methanol / 0.33 h / 50 °C 6: pyridine View Scheme