acetic acid T=50°C; 0.5 h;

osmium(VIII) oxide; 4-methylmorpholine N-oxide in tetrahydrofuran; water; tert-butyl alcohol 22 h; Ambient temperature;

hydrogenchloride in tetrahydrofuran 3 h; Heating;

1: 67.8 percent / n-BuLi 2: 83.9 percent / H2, ethylenediamine / P2-nickel 3: m-CPBA 4: n-BuLi 5: acid View Scheme

trifluoroacetic acid in methanol 1 h;

1: 14.8 g / OsO4, N-methylmorpholine N-oxide, H2O / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / Ambient temperature 2: 88 percent / p-toluenesulfonic acid / 2 h / Ambient temperature 3: 14.0 g / p-toluenesulfonic acid / 2 h / Heating 4: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating 5: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 6: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h 7: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min 8: 93 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr 9: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature 10: 1.36 g / triethylamine / CH2Cl2 / 0.08 h / 0 °C 11: 80 percent / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature 12: 96 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature 13: 1.) CH3COOH, H2O, pyridine, 2.) 4-(N,N-dimethylamino)pyridine / 1.) reflux, 4 h, 2.) RT, 10 h 14: 90 percent / SOCl2 / pyridine / 0.5 h / Ambient temperature 15: 45 percent / H2 / 5percent rhodium om alumina / ethyl acetate / 2 h / 2432 Torr 16: 94 percent / 5percent KOH-MeOH / 1 h / Heating View Scheme

1: 21.7 g / pyridine / 1 h / Ambient temperature 2: 80 percent / LiBr / dimethylformamide / 1 h / 140 °C 3: 14.8 g / OsO4, N-methylmorpholine N-oxide, H2O / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / Ambient temperature 4: 88 percent / p-toluenesulfonic acid / 2 h / Ambient temperature 5: 14.0 g / p-toluenesulfonic acid / 2 h / Heating 6: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating 7: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 8: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h 9: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min 10: 93 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr 11: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature 12: 1.36 g / triethylamine / CH2Cl2 / 0.08 h / 0 °C 13: 80 percent / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature 14: 96 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature 15: 1.) CH3COOH, H2O, pyridine, 2.) 4-(N,N-dimethylamino)pyridine / 1.) reflux, 4 h, 2.) RT, 10 h 16: 90 percent / SOCl2 / pyridine / 0.5 h / Ambient temperature 17: 45 percent / H2 / 5percent rhodium om alumina / ethyl acetate / 2 h / 2432 Torr 18: 94 percent / 5percent KOH-MeOH / 1 h / Heating View Scheme

1: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h 3: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min 4: 93 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr 5: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature 6: 1.36 g / triethylamine / CH2Cl2 / 0.08 h / 0 °C 7: 80 percent / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature 8: 96 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature 9: 1.) CH3COOH, H2O, pyridine, 2.) 4-(N,N-dimethylamino)pyridine / 1.) reflux, 4 h, 2.) RT, 10 h 10: 90 percent / SOCl2 / pyridine / 0.5 h / Ambient temperature 11: 45 percent / H2 / 5percent rhodium om alumina / ethyl acetate / 2 h / 2432 Torr 12: 94 percent / 5percent KOH-MeOH / 1 h / Heating View Scheme

1: 88 percent / p-toluenesulfonic acid / 2 h / Ambient temperature 2: 14.0 g / p-toluenesulfonic acid / 2 h / Heating 3: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating 4: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 5: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h 6: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min 7: 93 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr 8: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature 9: 1.36 g / triethylamine / CH2Cl2 / 0.08 h / 0 °C 10: 80 percent / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature 11: 96 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature 12: 1.) CH3COOH, H2O, pyridine, 2.) 4-(N,N-dimethylamino)pyridine / 1.) reflux, 4 h, 2.) RT, 10 h 13: 90 percent / SOCl2 / pyridine / 0.5 h / Ambient temperature 14: 45 percent / H2 / 5percent rhodium om alumina / ethyl acetate / 2 h / 2432 Torr 15: 94 percent / 5percent KOH-MeOH / 1 h / Heating View Scheme

1: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h 2: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min 3: 93 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr 4: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature 5: 1.36 g / triethylamine / CH2Cl2 / 0.08 h / 0 °C 6: 80 percent / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature 7: 96 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature 8: 1.) CH3COOH, H2O, pyridine, 2.) 4-(N,N-dimethylamino)pyridine / 1.) reflux, 4 h, 2.) RT, 10 h 9: 90 percent / SOCl2 / pyridine / 0.5 h / Ambient temperature 10: 45 percent / H2 / 5percent rhodium om alumina / ethyl acetate / 2 h / 2432 Torr 11: 94 percent / 5percent KOH-MeOH / 1 h / Heating View Scheme