hydrogen; palladium on activated charcoal in methanol; ethyl acetate Ambient temperature;

1: 1.) dimethyldioxirane, 2.) p-TsOH / 1.) CH2Cl2, Me2CO, 0 deg C, 12 h, 2.) CH2Cl2, 0 deg C, 30 min 2: 100 percent / K2CO3 / acetone / 2 h / Heating 3: 100 percent / AlBr3 / acetonitrile / 0.83 h / 0 °C 4: 100 percent / H2 / 10percent Pd/C / ethyl acetate; methanol / Ambient temperature View Scheme

1: 100 percent / K2CO3 / acetone / 2 h / Heating 2: 100 percent / AlBr3 / acetonitrile / 0.83 h / 0 °C 3: 100 percent / H2 / 10percent Pd/C / ethyl acetate; methanol / Ambient temperature View Scheme

1: 100 percent / AlBr3 / acetonitrile / 0.83 h / 0 °C 2: 100 percent / H2 / 10percent Pd/C / ethyl acetate; methanol / Ambient temperature View Scheme

1: 77 percent / K2CO3 / acetone; dimethylformamide / 50 h / Heating 2: 10percent aq. NaOH / methanol / 0.5 h / Ambient temperature 3: K2CO3 / acetone / 3 h / Heating 4: H2 / 10percent Pd/C / methanol; ethyl acetate / Ambient temperature 5: pyridine 6: 1.) AcOH, BF3(g), 2.) pyridine / 1.) from 50 to 60 deg C, 5 h 7: 10percent aq. NaOH / methanol / 0.25 h / Ambient temperature 8: (i-Pr)2NEt / CH2Cl2 / 0.83 h / 5 °C 9: pyridine / 3 h / 60 - 70 °C 10: KOH, pyridine / 2 h / 60 °C 11: conc. H2SO4, HOAc / 1 h / 50 °C 12: 86 percent / K2CO3 / dimethylformamide / 0.08 h / 150 °C 13: 1.) dimethyldioxirane, 2.) p-TsOH / 1.) CH2Cl2, Me2CO, 0 deg C, 12 h, 2.) CH2Cl2, 0 deg C, 30 min 14: 100 percent / K2CO3 / acetone / 2 h / Heating 15: 100 percent / AlBr3 / acetonitrile / 0.83 h / 0 °C 16: 100 percent / H2 / 10percent Pd/C / ethyl acetate; methanol / Ambient temperature View Scheme

1: 4percent aq. NaOH, 6percent aq. H2O2 / methanol / 2 h / 50 °C 2: pyridine 3: 77 percent / K2CO3 / acetone; dimethylformamide / 50 h / Heating 4: 10percent aq. NaOH / methanol / 0.5 h / Ambient temperature 5: K2CO3 / acetone / 3 h / Heating 6: H2 / 10percent Pd/C / methanol; ethyl acetate / Ambient temperature 7: pyridine 8: 1.) AcOH, BF3(g), 2.) pyridine / 1.) from 50 to 60 deg C, 5 h 9: 10percent aq. NaOH / methanol / 0.25 h / Ambient temperature 10: (i-Pr)2NEt / CH2Cl2 / 0.83 h / 5 °C 11: pyridine / 3 h / 60 - 70 °C 12: KOH, pyridine / 2 h / 60 °C 13: conc. H2SO4, HOAc / 1 h / 50 °C 14: 86 percent / K2CO3 / dimethylformamide / 0.08 h / 150 °C 15: 1.) dimethyldioxirane, 2.) p-TsOH / 1.) CH2Cl2, Me2CO, 0 deg C, 12 h, 2.) CH2Cl2, 0 deg C, 30 min 16: 100 percent / K2CO3 / acetone / 2 h / Heating 17: 100 percent / AlBr3 / acetonitrile / 0.83 h / 0 °C 18: 100 percent / H2 / 10percent Pd/C / ethyl acetate; methanol / Ambient temperature View Scheme

1: pyridine / 3 h / 60 - 70 °C 2: KOH, pyridine / 2 h / 60 °C 3: conc. H2SO4, HOAc / 1 h / 50 °C 4: 86 percent / K2CO3 / dimethylformamide / 0.08 h / 150 °C 5: 1.) dimethyldioxirane, 2.) p-TsOH / 1.) CH2Cl2, Me2CO, 0 deg C, 12 h, 2.) CH2Cl2, 0 deg C, 30 min 6: 100 percent / K2CO3 / acetone / 2 h / Heating 7: 100 percent / AlBr3 / acetonitrile / 0.83 h / 0 °C 8: 100 percent / H2 / 10percent Pd/C / ethyl acetate; methanol / Ambient temperature View Scheme

1: 10percent aq. NaOH / methanol / 0.25 h / Ambient temperature 2: (i-Pr)2NEt / CH2Cl2 / 0.83 h / 5 °C 3: pyridine / 3 h / 60 - 70 °C 4: KOH, pyridine / 2 h / 60 °C 5: conc. H2SO4, HOAc / 1 h / 50 °C 6: 86 percent / K2CO3 / dimethylformamide / 0.08 h / 150 °C 7: 1.) dimethyldioxirane, 2.) p-TsOH / 1.) CH2Cl2, Me2CO, 0 deg C, 12 h, 2.) CH2Cl2, 0 deg C, 30 min 8: 100 percent / K2CO3 / acetone / 2 h / Heating 9: 100 percent / AlBr3 / acetonitrile / 0.83 h / 0 °C 10: 100 percent / H2 / 10percent Pd/C / ethyl acetate; methanol / Ambient temperature View Scheme

1: 86 percent / K2CO3 / dimethylformamide / 0.08 h / 150 °C 2: 1.) dimethyldioxirane, 2.) p-TsOH / 1.) CH2Cl2, Me2CO, 0 deg C, 12 h, 2.) CH2Cl2, 0 deg C, 30 min 3: 100 percent / K2CO3 / acetone / 2 h / Heating 4: 100 percent / AlBr3 / acetonitrile / 0.83 h / 0 °C 5: 100 percent / H2 / 10percent Pd/C / ethyl acetate; methanol / Ambient temperature View Scheme