in tetrahydrofuran T=-30°C; 1 h;

bis(acetylacetonate)nickel(II); diisobutylaluminium hydride in diethyl ether; toluene T=-5°C; 1.5 h;

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

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

1: 53 percent / FeSO4; H2O; Cu(OAc)2 2: 100 percent / K2CO3; MeOH 3: MnO2 / CH2Cl2 View Scheme

1: (i) Cu(OAc)2, FeSO4, AcOH, (ii) KOH, MeOH 2: CrO3, H2SO4 View Scheme

1: 100 percent / K2CO3; MeOH 2: MnO2 / CH2Cl2 View Scheme

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