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