sodium hydroxide in methanol 1 h; Heating;

1: 1.) Mg, I2 / 1.) anhydrous THF, 4 h, 60 deg C, 2.) THF 2: 97 percent / H2O, 10percent HCl / methanol / 1 h / Ambient temperature 3: 1.) t-BuOK / 1.) anhydrous THF, 30 min, RT, 2.) THF, RT, 24 h 4: 58 percent / LAH / diethyl ether / 6 h / -78 °C 5: 93 percent / m-CPBA (80 percent) / CH2Cl2 / 0.67 h / 0 °C 6: 97 percent / H2, 1M NaOH / 10percent Pd/C / ethanol / 6 h / -60 °C 7: 98 percent / ICl / CH2Cl2 / Ambient temperature 8: RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / Ambient temperature 9: 1.) ZnCl2, 2.) dichlorobis(triphenylphosphine)palladium(II), DIBALH / 1.) ether, THF, RT, 10 min, 2.) ether, THF, RT, 1.5 h View Scheme

1: 1.) t-BuOK / 1.) anhydrous THF, 30 min, RT, 2.) THF, RT, 24 h 2: 58 percent / LAH / diethyl ether / 6 h / -78 °C 3: 93 percent / m-CPBA (80 percent) / CH2Cl2 / 0.67 h / 0 °C 4: 97 percent / H2, 1M NaOH / 10percent Pd/C / ethanol / 6 h / -60 °C 5: 98 percent / ICl / CH2Cl2 / Ambient temperature 6: RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / Ambient temperature 7: 1.) ZnCl2, 2.) dichlorobis(triphenylphosphine)palladium(II), DIBALH / 1.) ether, THF, RT, 10 min, 2.) ether, THF, RT, 1.5 h View Scheme

1: 98 percent / TsOH / benzene / 20 h / Heating 2: 1.) Mg, I2 / 1.) anhydrous THF, 4 h, 60 deg C, 2.) THF 3: 97 percent / H2O, 10percent HCl / methanol / 1 h / Ambient temperature 4: 1.) t-BuOK / 1.) anhydrous THF, 30 min, RT, 2.) THF, RT, 24 h 5: 58 percent / LAH / diethyl ether / 6 h / -78 °C 6: 93 percent / m-CPBA (80 percent) / CH2Cl2 / 0.67 h / 0 °C 7: 97 percent / H2, 1M NaOH / 10percent Pd/C / ethanol / 6 h / -60 °C 8: 98 percent / ICl / CH2Cl2 / Ambient temperature 9: RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / Ambient temperature 10: 1.) ZnCl2, 2.) dichlorobis(triphenylphosphine)palladium(II), DIBALH / 1.) ether, THF, RT, 10 min, 2.) ether, THF, RT, 1.5 h View Scheme

1: 58 percent / LAH / diethyl ether / 6 h / -78 °C 2: 93 percent / m-CPBA (80 percent) / CH2Cl2 / 0.67 h / 0 °C 3: 97 percent / H2, 1M NaOH / 10percent Pd/C / ethanol / 6 h / -60 °C 4: 98 percent / ICl / CH2Cl2 / Ambient temperature 5: RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / Ambient temperature 6: 1.) ZnCl2, 2.) dichlorobis(triphenylphosphine)palladium(II), DIBALH / 1.) ether, THF, RT, 10 min, 2.) ether, THF, RT, 1.5 h View Scheme

1: 93 percent / m-CPBA (80 percent) / CH2Cl2 / 0.67 h / 0 °C 2: 97 percent / H2, 1M NaOH / 10percent Pd/C / ethanol / 6 h / -60 °C 3: 98 percent / ICl / CH2Cl2 / Ambient temperature 4: RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / Ambient temperature 5: 1.) ZnCl2, 2.) dichlorobis(triphenylphosphine)palladium(II), DIBALH / 1.) ether, THF, RT, 10 min, 2.) ether, THF, RT, 1.5 h View Scheme

1: 97 percent / H2O, 10percent HCl / methanol / 1 h / Ambient temperature 2: 1.) t-BuOK / 1.) anhydrous THF, 30 min, RT, 2.) THF, RT, 24 h 3: 58 percent / LAH / diethyl ether / 6 h / -78 °C 4: 93 percent / m-CPBA (80 percent) / CH2Cl2 / 0.67 h / 0 °C 5: 97 percent / H2, 1M NaOH / 10percent Pd/C / ethanol / 6 h / -60 °C 6: 98 percent / ICl / CH2Cl2 / Ambient temperature 7: RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / Ambient temperature 8: 1.) ZnCl2, 2.) dichlorobis(triphenylphosphine)palladium(II), DIBALH / 1.) ether, THF, RT, 10 min, 2.) ether, THF, RT, 1.5 h View Scheme

1: HCl / 1 h / Heating 2: 66 percent / aq. NaOH, n-Bu4N(HSO4) / CH2Cl2 / 4 h / Ambient temperature 3: 71 percent / aq. NaOH / methanol / 1 h / Heating View Scheme

1: 66 percent / aq. NaOH, n-Bu4N(HSO4) / CH2Cl2 / 4 h / Ambient temperature 2: 71 percent / aq. NaOH / methanol / 1 h / Heating View Scheme

1: concd HCl / methanol / 4 h / Heating 2: HCl / 2 h / Heating 3: 1.) aq. NaNO2, concd HCl, 2.) H3PO2 / 1.) DMF, 0 deg C, 2.) DMF, 0-5 deg C, 59 h 4: HCl / 1 h / Heating 5: 66 percent / aq. NaOH, n-Bu4N(HSO4) / CH2Cl2 / 4 h / Ambient temperature 6: 71 percent / aq. NaOH / methanol / 1 h / Heating View Scheme