sodium hydrogencarbonate in ethanol 1.5 h; Heating;

1: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C 2: NaHCO3 / aq. ethanol / Heating 4: N-methylmorpholine N-oxide, selenium dioxide 5: imidazole / dimethylformamide View Scheme

1: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C 2: NaHCO3 / aq. ethanol / Heating 4: N-methylmorpholine N-oxide, selenium dioxide 5: imidazole / dimethylformamide 6: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H View Scheme

1: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C 2: NaHCO3 / aq. ethanol / Heating 4: N-methylmorpholine N-oxide, selenium dioxide 5: imidazole / dimethylformamide 6: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 7: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 8: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme

1: sodium hydrogen carbonate / aq. ethanol / 1.5 h / Heating 2: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating 3: imidazole / dimethylformamide / 1.5 h / 20 °C 4: liq. SO2 / diethyl ether / 0.5 h / Heating 5: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C 6: 90 percent / NaHCO3 / ethanol / 1.5 h / Heating View Scheme

1: sodium hydrogen carbonate / aq. ethanol / 1.5 h / Heating 2: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating 3: imidazole / dimethylformamide / 1.5 h / 20 °C View Scheme

1: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C 2: NaHCO3 / aq. ethanol / Heating 4: N-methylmorpholine N-oxide, selenium dioxide 5: imidazole / dimethylformamide 6: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 7: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation View Scheme