1: Ph3As; CuI / BnPd(PPh3)2Cl / hexamethylphosphoric acid triamide; dimethylformamide / 3.5 h / 85 °C 2: Na2CO3; H2O / methanol / 2 h / 20 °C 3: 89 percent / diethyl azodicarboxylate; PPh3 / benzene; toluene / 0.5 h / 20 °C 4: TFA / CH2Cl2 / 0.25 h / 20 °C 5: pyrrolidine / methanol; acetonitrile / 0.08 h / 20 °C 6: pyrrolidine / methanol; acetonitrile / 4 h / Heating 7: 88 percent / PPh3 / CCl4; acetonitrile / 0.5 h / 70 °C 8: KOH / methanol / 0.75 h / 80 °C View Scheme

1.1: Ph3As; CuI / BnPd(PPh3)2Cl / hexamethylphosphoric acid triamide; dimethylformamide / 3.5 h / 85 °C 2.1: Na2CO3; H2O / methanol / 2 h / 20 °C 3.1: 89 percent / diethyl azodicarboxylate; PPh3 / benzene; toluene / 0.5 h / 20 °C 4.1: TFA / CH2Cl2 / 0.25 h / 20 °C 5.1: pyrrolidine / methanol; acetonitrile / 0.08 h / 20 °C 6.1: pyrrolidine / methanol; acetonitrile / 4 h / Heating 7.1: 88 percent / PPh3 / CCl4; acetonitrile / 0.5 h / 70 °C 8.1: KOH / methanol / 0.75 h / 80 °C 9.1: t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 1.5 h / 0 °C 10.1: 88 percent / (PhSeO)2O / benzene / 0.5 h / 80 °C 11.1: MCPBA; NaHCO3; H2O / methanol; CH2Cl2 / 0.08 h / 0 °C 12.1: NaBH3CN; aq. HCl / methanol; CH2Cl2 / 0.58 h / 0 - 20 °C / pH 3.0 12.2: NaHSO3; Na2CO3 / aq. methanol; CH2Cl2 / 0.5 h / 20 °C / pH 9 - 10 13.1: 91 percent / AcONa / 4 h / 20 °C View Scheme

1.1: Ph3As; CuI / BnPd(PPh3)2Cl / hexamethylphosphoric acid triamide; dimethylformamide / 3.5 h / 85 °C 2.1: Na2CO3; H2O / methanol / 2 h / 20 °C 3.1: 89 percent / diethyl azodicarboxylate; PPh3 / benzene; toluene / 0.5 h / 20 °C 4.1: TFA / CH2Cl2 / 0.25 h / 20 °C 5.1: pyrrolidine / methanol; acetonitrile / 0.08 h / 20 °C 6.1: pyrrolidine / methanol; acetonitrile / 4 h / Heating 7.1: 88 percent / PPh3 / CCl4; acetonitrile / 0.5 h / 70 °C 8.1: KOH / methanol / 0.75 h / 80 °C 9.1: t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 1.5 h / 0 °C 10.1: 88 percent / (PhSeO)2O / benzene / 0.5 h / 80 °C 11.1: MCPBA; NaHCO3; H2O / methanol; CH2Cl2 / 0.08 h / 0 °C 12.1: NaBH3CN; aq. HCl / methanol; CH2Cl2 / 0.58 h / 0 - 20 °C / pH 3.0 12.2: NaHSO3; Na2CO3 / aq. methanol; CH2Cl2 / 0.5 h / 20 °C / pH 9 - 10 View Scheme