1: water; ruthenium trichloride; sodium periodate / acetonitrile / 4 h / 20 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C 3: 4-(N,N-dimethlyamino)pyridine; triethylamine / tetrahydrofuran / 1 h / 0 °C 4: ammonium hydroxide / methanol / 25 h / |Reflux 5: palladium 10 on activated carbon; hydrogen / methanol; water / 24 h / 20 °C View Scheme

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C 2: 4-(N,N-dimethlyamino)pyridine; triethylamine / tetrahydrofuran / 1 h / 0 °C 3: ammonium hydroxide / methanol / 25 h / |Reflux 4: palladium 10 on activated carbon; hydrogen / methanol; water / 24 h / 20 °C View Scheme

1: potassium carbonate / ethanol / 20 h / 20 °C 2: triethylamine / dichloromethane / 1 h / 0 °C 3: trifluoroacetic acid; water / 8 h / 20 °C 4: sodium azide; acetic acid / dimethyl sulfoxide / 2 h / 85 °C 5: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 5 h / 20 °C 6: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -10 °C 7: 4-(N,N-dimethlyamino)pyridine; triethylamine / ethyl acetate / 1 h / 0 °C 8: water; ruthenium trichloride; sodium periodate / acetonitrile / 4 h / 20 °C 9: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C 10: 4-(N,N-dimethlyamino)pyridine; triethylamine / tetrahydrofuran / 1 h / 0 °C 11: ammonium hydroxide / methanol / 25 h / |Reflux 12: palladium 10 on activated carbon; hydrogen / methanol; water / 24 h / 20 °C View Scheme

1: ammonium hydroxide / methanol / 25 h / |Reflux 2: palladium 10 on activated carbon; hydrogen / methanol; water / 24 h / 20 °C View Scheme

1: triethylamine / dichloromethane / 1 h / 0 °C 2: trifluoroacetic acid; water / 8 h / 20 °C 3: sodium azide; acetic acid / dimethyl sulfoxide / 2 h / 85 °C 4: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 5 h / 20 °C 5: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -10 °C 6: 4-(N,N-dimethlyamino)pyridine; triethylamine / ethyl acetate / 1 h / 0 °C 7: water; ruthenium trichloride; sodium periodate / acetonitrile / 4 h / 20 °C 8: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C 9: 4-(N,N-dimethlyamino)pyridine; triethylamine / tetrahydrofuran / 1 h / 0 °C 10: ammonium hydroxide / methanol / 25 h / |Reflux 11: palladium 10 on activated carbon; hydrogen / methanol; water / 24 h / 20 °C View Scheme

1: trifluoroacetic acid; water / 8 h / 20 °C 2: sodium azide; acetic acid / dimethyl sulfoxide / 2 h / 85 °C 3: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 5 h / 20 °C 4: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -10 °C 5: 4-(N,N-dimethlyamino)pyridine; triethylamine / ethyl acetate / 1 h / 0 °C 6: water; ruthenium trichloride; sodium periodate / acetonitrile / 4 h / 20 °C 7: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C 8: 4-(N,N-dimethlyamino)pyridine; triethylamine / tetrahydrofuran / 1 h / 0 °C 9: ammonium hydroxide / methanol / 25 h / |Reflux 10: palladium 10 on activated carbon; hydrogen / methanol; water / 24 h / 20 °C View Scheme

1: 55 percent / OsO4, Et3BuN(1+)*Cl(1-) / 2-methyl-propan-2-ol; CHCl3; H2O / 16 h / 50 °C 2: 50 percent / Na, NH3 (liq.) / 7 h / -78 °C View Scheme

1: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 16 h / -20 - 0 °C 2: 55 percent / OsO4, Et3BuN(1+)*Cl(1-) / 2-methyl-propan-2-ol; CHCl3; H2O / 16 h / 50 °C 3: 50 percent / Na, NH3 (liq.) / 7 h / -78 °C View Scheme

1: 64 g / sodium borohydride / H2O / 2 h / Ambient temperature 2: 42.7 g / barium hydroxide / H2O / 3 h / 70 - 80 °C View Scheme

1: 565 mg / sodium borohydride / H2O / 2 h 2: 42.7 g / barium hydroxide / H2O / 3 h / 70 - 80 °C View Scheme