1.1: HCl / methanol / 2 h / 70 °C 2.1: NaNO2; aq. HCl / ethyl acetate / -15 °C 2.2: KI / ethyl acetate / 0.25 h / -15 °C 3.1: 83 percent / BnEt3NCl / Pd(OAc)2 / dimethylformamide / 2 h / 50 °C 4.1: NaBH4 / methanol / 0.5 h / -15 °C 5.1: pyridine / 0.25 h / 20 °C 6.1: Zn; AcOH / CH2Cl2 / 0.5 h / 20 °C 7.1: Ac2O / CH2Cl2 / 0.5 h / 0 °C 8.1: 89 percent / POCl3; pyridine / CH2Cl2 / 0.67 h / 0 °C 9.1: n-Bu3SnH; AIBN / acetonitrile / 0.5 h / 80 °C 9.2: I2 / acetonitrile / 0.33 h / 20 °C 10.1: Et3N; DMAP / acetonitrile / 1 h / 20 °C 11.1: Ph3As; CuI / BnPd(PPh3)2Cl / hexamethylphosphoric acid triamide; dimethylformamide / 3.5 h / 85 °C 12.1: Na2CO3; H2O / methanol / 2 h / 20 °C 13.1: 89 percent / diethyl azodicarboxylate; PPh3 / benzene; toluene / 0.5 h / 20 °C 14.1: TFA / CH2Cl2 / 0.25 h / 20 °C 15.1: pyrrolidine / methanol; acetonitrile / 0.08 h / 20 °C 16.1: pyrrolidine / methanol; acetonitrile / 4 h / Heating 17.1: 88 percent / PPh3 / CCl4; acetonitrile / 0.5 h / 70 °C 18.1: KOH / methanol / 0.75 h / 80 °C View Scheme

1.1: HCl / methanol / 2 h / 70 °C 2.1: NaNO2; aq. HCl / ethyl acetate / -15 °C 2.2: KI / ethyl acetate / 0.25 h / -15 °C 3.1: 83 percent / BnEt3NCl / Pd(OAc)2 / dimethylformamide / 2 h / 50 °C 4.1: NaBH4 / methanol / 0.5 h / -15 °C 5.1: pyridine / 0.25 h / 20 °C 6.1: Zn; AcOH / CH2Cl2 / 0.5 h / 20 °C 7.1: Ac2O / CH2Cl2 / 0.5 h / 0 °C 8.1: 89 percent / POCl3; pyridine / CH2Cl2 / 0.67 h / 0 °C 9.1: n-Bu3SnH; AIBN / acetonitrile / 0.5 h / 80 °C 9.2: I2 / acetonitrile / 0.33 h / 20 °C 10.1: Et3N; DMAP / acetonitrile / 1 h / 20 °C 11.1: Ph3As; CuI / BnPd(PPh3)2Cl / hexamethylphosphoric acid triamide; dimethylformamide / 3.5 h / 85 °C 12.1: Na2CO3; H2O / methanol / 2 h / 20 °C 13.1: 89 percent / diethyl azodicarboxylate; PPh3 / benzene; toluene / 0.5 h / 20 °C 14.1: TFA / CH2Cl2 / 0.25 h / 20 °C 15.1: pyrrolidine / methanol; acetonitrile / 0.08 h / 20 °C 16.1: pyrrolidine / methanol; acetonitrile / 4 h / Heating 17.1: 88 percent / PPh3 / CCl4; acetonitrile / 0.5 h / 70 °C 18.1: KOH / methanol / 0.75 h / 80 °C 19.1: t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 1.5 h / 0 °C 20.1: 88 percent / (PhSeO)2O / benzene / 0.5 h / 80 °C 21.1: MCPBA; NaHCO3; H2O / methanol; CH2Cl2 / 0.08 h / 0 °C 22.1: NaBH3CN; aq. HCl / methanol; CH2Cl2 / 0.58 h / 0 - 20 °C / pH 3.0 22.2: NaHSO3; Na2CO3 / aq. methanol; CH2Cl2 / 0.5 h / 20 °C / pH 9 - 10 23.1: 91 percent / AcONa / 4 h / 20 °C View Scheme

1.1: HCl / methanol / 2 h / 70 °C 2.1: NaNO2; aq. HCl / ethyl acetate / -15 °C 2.2: KI / ethyl acetate / 0.25 h / -15 °C 3.1: 83 percent / BnEt3NCl / Pd(OAc)2 / dimethylformamide / 2 h / 50 °C 4.1: NaBH4 / methanol / 0.5 h / -15 °C 5.1: pyridine / 0.25 h / 20 °C 6.1: Zn; AcOH / CH2Cl2 / 0.5 h / 20 °C 7.1: Ac2O / CH2Cl2 / 0.5 h / 0 °C 8.1: 89 percent / POCl3; pyridine / CH2Cl2 / 0.67 h / 0 °C 9.1: n-Bu3SnH; AIBN / acetonitrile / 0.5 h / 80 °C 9.2: I2 / acetonitrile / 0.33 h / 20 °C 10.1: Et3N; DMAP / acetonitrile / 1 h / 20 °C 11.1: Ph3As; CuI / BnPd(PPh3)2Cl / hexamethylphosphoric acid triamide; dimethylformamide / 3.5 h / 85 °C 12.1: Na2CO3; H2O / methanol / 2 h / 20 °C 13.1: 89 percent / diethyl azodicarboxylate; PPh3 / benzene; toluene / 0.5 h / 20 °C 14.1: TFA / CH2Cl2 / 0.25 h / 20 °C 15.1: pyrrolidine / methanol; acetonitrile / 0.08 h / 20 °C 16.1: pyrrolidine / methanol; acetonitrile / 4 h / Heating 17.1: 88 percent / PPh3 / CCl4; acetonitrile / 0.5 h / 70 °C 18.1: KOH / methanol / 0.75 h / 80 °C 19.1: t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 1.5 h / 0 °C 20.1: 88 percent / (PhSeO)2O / benzene / 0.5 h / 80 °C 21.1: MCPBA; NaHCO3; H2O / methanol; CH2Cl2 / 0.08 h / 0 °C 22.1: NaBH3CN; aq. HCl / methanol; CH2Cl2 / 0.58 h / 0 - 20 °C / pH 3.0 22.2: NaHSO3; Na2CO3 / aq. methanol; CH2Cl2 / 0.5 h / 20 °C / pH 9 - 10 View Scheme