AG-50WX4(resin) in methanol 16 h; Ambient temperature;

1: quinoline, H2 / 10percent Pd/BaSO4 / methanol / 0.13 h / 93.09 Torr 2: 95 percent / (4-dimethylamino)pyridine (DMAP), pyridine / 0 °C 3: 1.) Cu2I2 / 1.) Et2O, 0 deg C, 30 min, 2.) Et2O, RT, 48 h 4: 100 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 5: 100 percent / pyridinium dichromate, pyridinium p-toluenesulfonate / CH2Cl2 / 24 h / Ambient temperature 6: 1.) n-BuLi / 1.) hexane, THF, -70 deg C, 30 min, 2.) THF, -70 deg C, 90 min 7: 76 percent / AG-50WX4(resin) / methanol / 16 h / Ambient temperature View Scheme

1: 90 percent / pyridine 2: 91 percent / potassium tert-butylate / dimethylformamide 3: 99 percent / Na2WO4, H2O2 / 70 °C 4: 95 percent / pyridinium p-toluenesulphonate / CH2Cl2 5: 1) lithium diisopropylamide / 1) THF, -78 deg C 6: 52 percent / 5percent Na-Hg, Na2HPO4 / 0 °C 7: 95 percent / 95percent ethanol / pyridinium p-toluenesulphonate / 40 °C 8: irradiation followed by thermal isomerization View Scheme

1: 99 percent / Na2WO4, H2O2 / 70 °C 2: 95 percent / pyridinium p-toluenesulphonate / CH2Cl2 3: 1) lithium diisopropylamide / 1) THF, -78 deg C 4: 52 percent / 5percent Na-Hg, Na2HPO4 / 0 °C 5: 95 percent / 95percent ethanol / pyridinium p-toluenesulphonate / 40 °C 6: irradiation followed by thermal isomerization View Scheme

2: 90 percent / pyridine 3: 91 percent / potassium tert-butylate / dimethylformamide 4: 99 percent / Na2WO4, H2O2 / 70 °C 5: 95 percent / pyridinium p-toluenesulphonate / CH2Cl2 6: 1) lithium diisopropylamide / 1) THF, -78 deg C 7: 52 percent / 5percent Na-Hg, Na2HPO4 / 0 °C 8: 95 percent / 95percent ethanol / pyridinium p-toluenesulphonate / 40 °C 9: irradiation followed by thermal isomerization View Scheme

1: 95 percent / pyridinium p-toluenesulphonate / CH2Cl2 2: 1) lithium diisopropylamide / 1) THF, -78 deg C 3: 52 percent / 5percent Na-Hg, Na2HPO4 / 0 °C 4: 95 percent / 95percent ethanol / pyridinium p-toluenesulphonate / 40 °C 5: irradiation followed by thermal isomerization View Scheme

1: 92 percent / NaH / dimethylsulfoxide / Ambient temperature 2: 93 percent / diethyl ether / -20 °C 4: 90 percent / pyridine 5: 91 percent / potassium tert-butylate / dimethylformamide 6: 99 percent / Na2WO4, H2O2 / 70 °C 7: 95 percent / pyridinium p-toluenesulphonate / CH2Cl2 8: 1) lithium diisopropylamide / 1) THF, -78 deg C 9: 52 percent / 5percent Na-Hg, Na2HPO4 / 0 °C 10: 95 percent / 95percent ethanol / pyridinium p-toluenesulphonate / 40 °C 11: irradiation followed by thermal isomerization View Scheme

1: 93 percent / diethyl ether / -20 °C 3: 90 percent / pyridine 4: 91 percent / potassium tert-butylate / dimethylformamide 5: 99 percent / Na2WO4, H2O2 / 70 °C 6: 95 percent / pyridinium p-toluenesulphonate / CH2Cl2 7: 1) lithium diisopropylamide / 1) THF, -78 deg C 8: 52 percent / 5percent Na-Hg, Na2HPO4 / 0 °C 9: 95 percent / 95percent ethanol / pyridinium p-toluenesulphonate / 40 °C 10: irradiation followed by thermal isomerization View Scheme

1: 91 percent / potassium tert-butylate / dimethylformamide 2: 99 percent / Na2WO4, H2O2 / 70 °C 3: 95 percent / pyridinium p-toluenesulphonate / CH2Cl2 4: 1) lithium diisopropylamide / 1) THF, -78 deg C 5: 52 percent / 5percent Na-Hg, Na2HPO4 / 0 °C 6: 95 percent / 95percent ethanol / pyridinium p-toluenesulphonate / 40 °C 7: irradiation followed by thermal isomerization View Scheme

1: oxalyl chloride, triethylamine / dimethylsulfoxide 2: 1) lithium diisopropylamide / 1) THF, -78 deg C 3: 52 percent / 5percent Na-Hg, Na2HPO4 / 0 °C 4: 95 percent / 95percent ethanol / pyridinium p-toluenesulphonate / 40 °C 5: irradiation followed by thermal isomerization View Scheme