hydrogen; palladium on activated charcoal in methanol; ethyl acetate

1: pyridine / 2 h / 60 - 80 °C 2: KOH, pyridine / 2 h / 60 - 70 °C 3: H2SO4, AcOH / 1 h / 50 °C 4: 100 percent / N,N-diisopropylethylamine / CH2Cl2 5: 1.) dimethyldioxirane, 2.) TsOH / 1.) acetone, CH2Cl2, 0 deg C, 12 h, 2.) CH2Cl2, 0 deg C, 20 min 6: conc. HCl / acetic acid / 2 h / Ambient temperature 7: K2CO3 / acetone / Heating 8: AlBr3 / acetonitrile / 0.67 h / 0 °C 9: H2 / 10percent Pd/C / methanol; ethyl acetate View Scheme

1: N,N-diisopropylethylamine / CH2Cl2 / 4 h / Ambient temperature 2: pyridine / 2 h / 60 - 80 °C 3: KOH, pyridine / 2 h / 60 - 70 °C 4: H2SO4, AcOH / 1 h / 50 °C 5: 100 percent / N,N-diisopropylethylamine / CH2Cl2 6: 1.) dimethyldioxirane, 2.) TsOH / 1.) acetone, CH2Cl2, 0 deg C, 12 h, 2.) CH2Cl2, 0 deg C, 20 min 7: conc. HCl / acetic acid / 2 h / Ambient temperature 8: K2CO3 / acetone / Heating 9: AlBr3 / acetonitrile / 0.67 h / 0 °C 10: H2 / 10percent Pd/C / methanol; ethyl acetate View Scheme

1: pyridine / 2 h / 60 - 80 °C 2: KOH, pyridine / 2 h / 60 - 70 °C 3: H2SO4, AcOH / 1 h / 50 °C 4: 100 percent / N,N-diisopropylethylamine / CH2Cl2 5: 1.) dimethyldioxirane, 2.) TsOH / 1.) acetone, CH2Cl2, 0 deg C, 12 h, 2.) CH2Cl2, 0 deg C, 20 min 6: conc. HCl / acetic acid / 2 h / Ambient temperature 7: K2CO3 / acetone / Heating 8: AlBr3 / acetonitrile / 0.67 h / 0 °C 9: H2 / 10percent Pd/C / methanol; ethyl acetate View Scheme

1: 100 percent / N,N-diisopropylethylamine / CH2Cl2 2: 1.) dimethyldioxirane, 2.) TsOH / 1.) acetone, CH2Cl2, 0 deg C, 12 h, 2.) CH2Cl2, 0 deg C, 20 min 3: conc. HCl / acetic acid / 2 h / Ambient temperature 4: K2CO3 / acetone / Heating 5: AlBr3 / acetonitrile / 0.67 h / 0 °C 6: H2 / 10percent Pd/C / methanol; ethyl acetate View Scheme

1: K2CO3 / acetone / Heating 2: AlBr3 / acetonitrile / 0.67 h / 0 °C 3: H2 / 10percent Pd/C / methanol; ethyl acetate View Scheme

1: AlBr3 / acetonitrile / 0.67 h / 0 °C 2: H2 / 10percent Pd/C / methanol; ethyl acetate View Scheme

1: 1.) dimethyldioxirane, 2.) TsOH / 1.) acetone, CH2Cl2, 0 deg C, 12 h, 2.) CH2Cl2, 0 deg C, 20 min 2: conc. HCl / acetic acid / 2 h / Ambient temperature 3: K2CO3 / acetone / Heating 4: AlBr3 / acetonitrile / 0.67 h / 0 °C 5: H2 / 10percent Pd/C / methanol; ethyl acetate View Scheme

1: conc. HCl / acetic acid / 2 h / Ambient temperature 2: K2CO3 / acetone / Heating 3: AlBr3 / acetonitrile / 0.67 h / 0 °C 4: H2 / 10percent Pd/C / methanol; ethyl acetate View Scheme

1: KOH, pyridine / 2 h / 60 - 70 °C 2: H2SO4, AcOH / 1 h / 50 °C 3: 100 percent / N,N-diisopropylethylamine / CH2Cl2 4: 1.) dimethyldioxirane, 2.) TsOH / 1.) acetone, CH2Cl2, 0 deg C, 12 h, 2.) CH2Cl2, 0 deg C, 20 min 5: conc. HCl / acetic acid / 2 h / Ambient temperature 6: K2CO3 / acetone / Heating 7: AlBr3 / acetonitrile / 0.67 h / 0 °C 8: H2 / 10percent Pd/C / methanol; ethyl acetate View Scheme