1: 5.1 g / pyridine / 15 h / Ambient temperature 2: 26.2 g / pyridine / 16 h / Ambient temperature 3: 16.9 g / sodium iodide / acetic anhydride / 0.5 h / 120 - 130 °C 4: 11.6 g / silver fluoride / pyridine / 3.5 h / 20 - 25 °C 5: 3.5 g / 5 M ammonium hydroxide / ethanol / 96 h / Ambient temperature 6: 2.4 g / bromine / methanol / 1 h / 0 - 5 °C 7: 104 mg / barium hydroxide / H2O / 5 h / 60 - 70 °C View Scheme

1: 136 g / bromine / methanol / 1 h / 0 - 5 °C 2: 64 g / sodium borohydride / H2O / 2 h / Ambient temperature 3: 42.7 g / barium hydroxide / H2O / 3 h / 70 - 80 °C View Scheme

1: 3.5 g / 5 M ammonium hydroxide / ethanol / 96 h / Ambient temperature 2: 2.4 g / bromine / methanol / 1 h / 0 - 5 °C 3: 104 mg / barium hydroxide / H2O / 5 h / 60 - 70 °C View Scheme

1: 11.6 g / silver fluoride / pyridine / 3.5 h / 20 - 25 °C 2: 3.5 g / 5 M ammonium hydroxide / ethanol / 96 h / Ambient temperature 3: 2.4 g / bromine / methanol / 1 h / 0 - 5 °C 4: 104 mg / barium hydroxide / H2O / 5 h / 60 - 70 °C View Scheme

1: 26.2 g / pyridine / 16 h / Ambient temperature 2: 16.9 g / sodium iodide / acetic anhydride / 0.5 h / 120 - 130 °C 3: 11.6 g / silver fluoride / pyridine / 3.5 h / 20 - 25 °C 4: 3.5 g / 5 M ammonium hydroxide / ethanol / 96 h / Ambient temperature 5: 2.4 g / bromine / methanol / 1 h / 0 - 5 °C 6: 104 mg / barium hydroxide / H2O / 5 h / 60 - 70 °C View Scheme

1: 16.9 g / sodium iodide / acetic anhydride / 0.5 h / 120 - 130 °C 2: 11.6 g / silver fluoride / pyridine / 3.5 h / 20 - 25 °C 3: 3.5 g / 5 M ammonium hydroxide / ethanol / 96 h / Ambient temperature 4: 2.4 g / bromine / methanol / 1 h / 0 - 5 °C 5: 104 mg / barium hydroxide / H2O / 5 h / 60 - 70 °C View Scheme

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

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

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

1.1: thionyl chloride / 0.5 h / 20 °C 1.2: 0 - 20 °C 2.1: potassium carbonate / ethanol / 20 h / 20 °C 3.1: triethylamine / dichloromethane / 1 h / 0 °C 4.1: trifluoroacetic acid; water / 8 h / 20 °C 5.1: sodium azide; acetic acid / dimethyl sulfoxide / 2 h / 85 °C 6.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 5 h / 20 °C 7.1: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -10 °C 8.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / ethyl acetate / 1 h / 0 °C 9.1: water; ruthenium trichloride; sodium periodate / acetonitrile / 4 h / 20 °C 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C 11.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / tetrahydrofuran / 1 h / 0 °C 12.1: ammonium hydroxide / methanol / 25 h / |Reflux 13.1: palladium 10 on activated carbon; hydrogen / methanol; water / 24 h / 20 °C View Scheme