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

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 5 steps 1: 14.0 g / p-toluenesulfonic acid / 2 h / Heating2: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating3: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature4: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h5: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min  

Multi-step reaction with 6 steps 1: 14.0 g / p-toluenesulfonic acid / 2 h / Heating2: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating3: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature4: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h5: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min6: 93 percent / triethylamine, 4-pyrrolidinopyridine / CH2Cl2 / 1 h / Ambient temperature  

Multi-step reaction with 8 steps 1: 14.0 g / p-toluenesulfonic acid / 2 h / Heating2: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating3: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature4: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h5: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min6: 93 percent / triethylamine, 4-pyrrolidinopyridine / CH2Cl2 / 1 h / Ambient temperature7: 71 percent / DBU / benzene / 0.5 h / Heating8: 92 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr  

Multi-step reaction with 9 steps 1: 14.0 g / p-toluenesulfonic acid / 2 h / Heating2: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating3: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature4: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h5: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min6: 93 percent / triethylamine, 4-pyrrolidinopyridine / CH2Cl2 / 1 h / Ambient temperature7: 71 percent / DBU / benzene / 0.5 h / Heating8: 92 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr9: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature  

Multi-step reaction with 10 steps 1: 14.0 g / p-toluenesulfonic acid / 2 h / Heating2: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating3: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature4: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h5: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min6: 93 percent / triethylamine, 4-pyrrolidinopyridine / CH2Cl2 / 1 h / Ambient temperature7: 71 percent / DBU / benzene / 0.5 h / Heating8: 92 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr9: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature10: 83 mg / triethylamine / CH2Cl2 / 0.17 h / 0 °C  

Multi-step reaction with 11 steps 1: 14.0 g / p-toluenesulfonic acid / 2 h / Heating2: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating3: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature4: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h5: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min6: 93 percent / triethylamine, 4-pyrrolidinopyridine / CH2Cl2 / 1 h / Ambient temperature7: 71 percent / DBU / benzene / 0.5 h / Heating8: 92 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr9: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature10: 83 mg / triethylamine / CH2Cl2 / 0.17 h / 0 °C11: 65 mg / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature  

Multi-step reaction with 12 steps 1: 14.0 g / p-toluenesulfonic acid / 2 h / Heating2: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating3: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature4: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h5: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min6: 93 percent / triethylamine, 4-pyrrolidinopyridine / CH2Cl2 / 1 h / Ambient temperature7: 71 percent / DBU / benzene / 0.5 h / Heating8: 92 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr9: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature10: 83 mg / triethylamine / CH2Cl2 / 0.17 h / 0 °C11: 65 mg / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature12: 82 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature  

Multi-step reaction with 6 steps 1: 14.0 g / p-toluenesulfonic acid / 2 h / Heating2: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating3: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature4: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h5: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min6: 93 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr