lithium iodide in tetrahydrofuran T=20 - 44°C; Reflux;

1: potassium t-butoxide / dimethylformamide / 4 h / Ambient temperature 2: WO3, 50percent NaOH, 30percent H2O2 / H2O; ethanol / 0.67 h / 60 - 75 °C 3: 92 percent / PPTS / CH2Cl2 / 4 h / Ambient temperature 4: n-butyllithium / hexane; tetrahydrofuran / 1 h / -70 - -60 °C 5: Na2HPO4, 5percent sodium amalgam / methanol / 0 deg C, 15 h, then RT, 3 h 6: PPTS / aq. ethanol / 1 h / 50 °C 7: LiAlH4 / tetrahydrofuran / 1.5 h / Heating 8: diethyl ether; tetrahydrofuran / 0.05 h / Irradiation 9: ethanol / 1 h / Heating View Scheme

1: 85 percent / LiI / tetrahydrofuran / 0.25 h / Heating 2: 100 percent / acetonitrile / 40 h / Heating 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: potassium t-butoxide / dimethylformamide / 4 h / Ambient temperature 2: WO3, 50percent NaOH, 30percent H2O2 / H2O; ethanol / 0.67 h / 60 - 75 °C 3: 92 percent / PPTS / CH2Cl2 / 4 h / Ambient temperature View Scheme

1: potassium t-butoxide / dimethylformamide / 4 h / Ambient temperature 2: WO3, 50percent NaOH, 30percent H2O2 / H2O; ethanol / 0.67 h / 60 - 75 °C View Scheme