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

Multi-step reaction with 4 steps 1: 14.8 g / OsO4, N-methylmorpholine N-oxide, H2O / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / Ambient temperature2: 88 percent / p-toluenesulfonic acid / 2 h / Ambient temperature3: 14.0 g / p-toluenesulfonic acid / 2 h / Heating4: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating  

Multi-step reaction with 6 steps 1: 21.7 g / pyridine / 1 h / Ambient temperature2: 80 percent / LiBr / dimethylformamide / 1 h / 140 °C3: 14.8 g / OsO4, N-methylmorpholine N-oxide, H2O / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / Ambient temperature4: 88 percent / p-toluenesulfonic acid / 2 h / Ambient temperature5: 14.0 g / p-toluenesulfonic acid / 2 h / Heating6: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating  

Multi-step reaction with 7 steps 1: 18.1 g / 5percent NaOH aq. / methanol; CH2Cl2 / 1 h / Ambient temperature2: 21.7 g / pyridine / 1 h / Ambient temperature3: 80 percent / LiBr / dimethylformamide / 1 h / 140 °C4: 14.8 g / OsO4, N-methylmorpholine N-oxide, H2O / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / Ambient temperature5: 88 percent / p-toluenesulfonic acid / 2 h / Ambient temperature6: 14.0 g / p-toluenesulfonic acid / 2 h / Heating7: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating  

Multi-step reaction with 5 steps 1: 80 percent / LiBr / dimethylformamide / 1 h / 140 °C2: 14.8 g / OsO4, N-methylmorpholine N-oxide, H2O / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / Ambient temperature3: 88 percent / p-toluenesulfonic acid / 2 h / Ambient temperature4: 14.0 g / p-toluenesulfonic acid / 2 h / Heating5: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating  

With  methanol; sodium hydroxide 1 h;  Heating;   

Multi-step reaction with 2 steps 1: 14.0 g / p-toluenesulfonic acid / 2 h / Heating2: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating  

Multi-step reaction with 3 steps 1: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature2: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h3: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min  

Multi-step reaction with 4 steps 1: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature2: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h3: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min4: 93 percent / triethylamine, 4-pyrrolidinopyridine / CH2Cl2 / 1 h / Ambient temperature  

Multi-step reaction with 6 steps 1: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature2: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h3: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min4: 93 percent / triethylamine, 4-pyrrolidinopyridine / CH2Cl2 / 1 h / Ambient temperature5: 71 percent / DBU / benzene / 0.5 h / Heating6: 92 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr