1: 95 percent / PDC / CH2Cl2 / 20 °C 2: 92 percent / CeCl3*7H2O; NaBH4 / methanol / 0.5 h / -78 °C 3: 43 percent / lipase PS, Pseudomonas sp. AMANO / various solvent(s) / 2 h / 20 °C 4: 95 percent / K2CO3 / methanol / 1.5 h / 20 °C 5: 99 percent / imidazole / dimethylformamide / 3 h / 20 °C 6: 90 percent / NMO / aq. OsO4 / tetrahydrofuran / 72 h / 20 °C 7: 97 percent / PPTS / CH2Cl2 / 24 h / 20 °C 8: 96 percent / H2 / 10 percent Pd/C; CHCl3 / ethyl acetate / 17 h / 20 °C 9: 97 percent / Dess-Martin reagent / CH2Cl2 / 0.5 h / 20 °C 10: 78 percent / acetic acid / 96 h / 60 °C View Scheme

toluene-4-sulfonic acid T=105°C;

1: 95 percent / PDC / CH2Cl2 / 20 °C 2: 92 percent / CeCl3*7H2O; NaBH4 / methanol / 0.5 h / -78 °C 3: 43 percent / lipase PS, Pseudomonas sp. AMANO / various solvent(s) / 2 h / 20 °C 4: 95 percent / K2CO3 / methanol / 1.5 h / 20 °C 5: 99 percent / imidazole / dimethylformamide / 3 h / 20 °C 6: 90 percent / NMO / aq. OsO4 / tetrahydrofuran / 72 h / 20 °C 7: 97 percent / PPTS / CH2Cl2 / 24 h / 20 °C 8: 98 percent / TBAF / tetrahydrofuran / 2.5 h / 20 °C 9: 96 percent / Dess-Martin reagent / CH2Cl2 / 0.5 h / 20 °C 10: 76 percent / acetic acid / 96 h / 60 °C View Scheme

molecular sieve; pyridinium chlorochromate in dichloromethane 1 h; Ambient temperature;