1: K2CO3 / ethanol / 10 h / Heating 2: NaOEt / ethanol; tetrahydrofuran / a) -15 deg C, 3 h, b) 4 deg C, 12 h 3: xylene / 3 h / Heating 4: 93 percent / KOH / ethanol / 1.5 h / Heating 5: 73 percent / copper chromite / quinoline / 3 h / 230 °C 6: acetic acid / CH2Cl2 / 2 h / Ambient temperature 7: 1.) iodomethane / 1.) THF, from 0 deg C to 4 deg C, 30 h, 2.) water, 80 deg C, 3.5 h 8: H2, NH3 / Raney nickel / ethanol / 48 h / 2508 Torr / Ambient temperature 9: 1.) NaOEt / 1.) ethanol, 0 deg C, 1 h, 2.) ethanol, RT, 3 h 10: H2 / 10percent Pd/C / ethanol / 48 h / 2508 Torr / Ambient temperature 11: Fremy's salt, aq. KH2PO4 / acetone / 4 h / 0 °C 12: 1.) t-BuOK / 1.) THF, 0 deg C, 1 h, 2.) THF, RT, 3 h 13: p-toluenesulfonic acid / acetonitrile / 5 h / Ambient temperature 14: NaHCO3 / ethanol / 3 h / Heating 15: CH2Cl2 / 3 h / Ambient temperature 16: PhI(OCOCF3)2 (PIFA) / various solvent(s) / 0.33 h / Ambient temperature View Scheme

1: NaOEt / ethanol; tetrahydrofuran / a) -15 deg C, 3 h, b) 4 deg C, 12 h 2: xylene / 3 h / Heating 3: 93 percent / KOH / ethanol / 1.5 h / Heating 4: 73 percent / copper chromite / quinoline / 3 h / 230 °C 5: acetic acid / CH2Cl2 / 2 h / Ambient temperature 6: 1.) iodomethane / 1.) THF, from 0 deg C to 4 deg C, 30 h, 2.) water, 80 deg C, 3.5 h 7: H2, NH3 / Raney nickel / ethanol / 48 h / 2508 Torr / Ambient temperature 8: 1.) NaOEt / 1.) ethanol, 0 deg C, 1 h, 2.) ethanol, RT, 3 h 9: H2 / 10percent Pd/C / ethanol / 48 h / 2508 Torr / Ambient temperature 10: Fremy's salt, aq. KH2PO4 / acetone / 4 h / 0 °C 11: 1.) t-BuOK / 1.) THF, 0 deg C, 1 h, 2.) THF, RT, 3 h 12: p-toluenesulfonic acid / acetonitrile / 5 h / Ambient temperature 13: NaHCO3 / ethanol / 3 h / Heating 14: CH2Cl2 / 3 h / Ambient temperature 15: PhI(OCOCF3)2 (PIFA) / various solvent(s) / 0.33 h / Ambient temperature View Scheme

1: H2 / 10percent Pd/C / ethanol / 48 h / 2508 Torr / Ambient temperature 2: Fremy's salt, aq. KH2PO4 / acetone / 4 h / 0 °C 3: 1.) t-BuOK / 1.) THF, 0 deg C, 1 h, 2.) THF, RT, 3 h 4: p-toluenesulfonic acid / acetonitrile / 5 h / Ambient temperature 5: NaHCO3 / ethanol / 3 h / Heating 6: CH2Cl2 / 3 h / Ambient temperature 7: PhI(OCOCF3)2 (PIFA) / various solvent(s) / 0.33 h / Ambient temperature View Scheme

electrochemical oxidation;

1: NaHCO3 / ethanol / 3 h / Heating 2: CH2Cl2 / 3 h / Ambient temperature 3: PhI(OCOCF3)2 (PIFA) / various solvent(s) / 0.33 h / Ambient temperature View Scheme

1: K2CO3 / dimethylformamide 2: Fe, HCl / H2O 3: ICl, Na2CO3 / diethyl ether; H2O 4: 86 percent / NaHCL3 / acetone; H2O 5: 89 percent / (o-MeC6H4)3P, Et3N / Pd(OAc)2 / acetonitrile / 3 h / Heating 6: LiAlH4 / diethyl ether 7: CH2Cl2 8: NaH / dimethylformamide 9: 100 percent / H2 / Pd/C / methanol 10: 82 percent / Fremy's salt / acetone; H2O 11: 1.) TFA, 2.) NaHCO3 / 1.) CH2Cl2, 2.) EtOH 12: CuCl2, Et3N, O2 / acetonitrile 13: NaOMe / methanol View Scheme

1: 86 percent / NaHCL3 / acetone; H2O 2: 89 percent / (o-MeC6H4)3P, Et3N / Pd(OAc)2 / acetonitrile / 3 h / Heating 3: LiAlH4 / diethyl ether 4: CH2Cl2 5: NaH / dimethylformamide 6: 100 percent / H2 / Pd/C / methanol 7: 82 percent / Fremy's salt / acetone; H2O 8: 1.) TFA, 2.) NaHCO3 / 1.) CH2Cl2, 2.) EtOH 9: CuCl2, Et3N, O2 / acetonitrile 10: NaOMe / methanol View Scheme

1: LiAlH4 / diethyl ether 2: CH2Cl2 3: NaH / dimethylformamide 4: 100 percent / H2 / Pd/C / methanol 5: 82 percent / Fremy's salt / acetone; H2O 6: 1.) TFA, 2.) NaHCO3 / 1.) CH2Cl2, 2.) EtOH 7: CuCl2, Et3N, O2 / acetonitrile 8: NaOMe / methanol View Scheme

1: 89 percent / (o-MeC6H4)3P, Et3N / Pd(OAc)2 / acetonitrile / 3 h / Heating 2: LiAlH4 / diethyl ether 3: CH2Cl2 4: NaH / dimethylformamide 5: 100 percent / H2 / Pd/C / methanol 6: 82 percent / Fremy's salt / acetone; H2O 7: 1.) TFA, 2.) NaHCO3 / 1.) CH2Cl2, 2.) EtOH 8: CuCl2, Et3N, O2 / acetonitrile 9: NaOMe / methanol View Scheme

1: NaH / dimethylformamide 2: 100 percent / H2 / Pd/C / methanol 3: 82 percent / Fremy's salt / acetone; H2O 4: 1.) TFA, 2.) NaHCO3 / 1.) CH2Cl2, 2.) EtOH 5: CuCl2, Et3N, O2 / acetonitrile 6: NaOMe / methanol View Scheme