silver; copper; zinc in methanol T=40°C; 5 h;

1: MeMgBr; CuBr*Me2S / tetrahydrofuran / 0 - 20 °C 2: 2,2-dimethoxypropane; TMSCl / 20 °C 3: MCPBA; NaHCO3 / CH2Cl2 / 0 - 20 °C 4: H2O / (R,R)-(salen)Co(III)(OAc) / diethyl ether / 0 - 20 °C 5: imidazole; Et3N / dimethylformamide / 0 - 20 °C 6: 100 percent / Et3N / Lindlar catalyst / hexane / 0 - 20 °C 7: 54 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 8: 50 percent / CrCl2 / tetrahydrofuran / 0 °C 9: CuI; NPrNH2 / Pd(PPh3)4 / benzene / 20 °C 10: pyridinium p-toluenesulfonate / methanol / 20 °C 11: aq. HCl / methanol / 0.25 h / 20 °C 12: 70 percent / Zn(Cu/Ag) / aq. methanol / 5 h / 40 °C View Scheme

1.1: n-BuLi / tetrahydrofuran / -78 - 0 °C 1.2: I2 / benzene / 20 °C 2.1: 83 percent / KF; 18-crown-6 / dimethylformamide / 20 °C 3.1: CuI; NPrNH2 / Pd(PPh3)4 / benzene / 20 °C 4.1: pyridinium p-toluenesulfonate / methanol / 20 °C 5.1: aq. HCl / methanol / 0.25 h / 20 °C 6.1: 70 percent / Zn(Cu/Ag) / aq. methanol / 5 h / 40 °C View Scheme

1.1: 70 percent / PCC; NaOAc / CH2Cl2 2.1: n-BuLi / tetrahydrofuran / -78 - 0 °C 2.2: I2 / benzene / 20 °C 3.1: 83 percent / KF; 18-crown-6 / dimethylformamide / 20 °C 4.1: CuI; NPrNH2 / Pd(PPh3)4 / benzene / 20 °C 5.1: pyridinium p-toluenesulfonate / methanol / 20 °C 6.1: aq. HCl / methanol / 0.25 h / 20 °C 7.1: 70 percent / Zn(Cu/Ag) / aq. methanol / 5 h / 40 °C View Scheme

1.1: NaN(TMS)2 / diethyl ether / -78 - 0 °C 2.1: 70 percent / PCC; NaOAc / CH2Cl2 3.1: n-BuLi / tetrahydrofuran / -78 - 0 °C 3.2: I2 / benzene / 20 °C 4.1: 83 percent / KF; 18-crown-6 / dimethylformamide / 20 °C 5.1: CuI; NPrNH2 / Pd(PPh3)4 / benzene / 20 °C 6.1: pyridinium p-toluenesulfonate / methanol / 20 °C 7.1: aq. HCl / methanol / 0.25 h / 20 °C 8.1: 70 percent / Zn(Cu/Ag) / aq. methanol / 5 h / 40 °C View Scheme

1.1: n-BuLi / tetrahydrofuran / -78 - 0 °C 1.2: I2 / benzene / 20 °C 2.1: 83 percent / KF; 18-crown-6 / dimethylformamide / 20 °C 3.1: CuI; NPrNH2 / Pd(PPh3)4 / benzene / 20 °C 4.1: pyridinium p-toluenesulfonate / methanol / 20 °C 5.1: aq. HCl / methanol / 0.25 h / 20 °C 6.1: 70 percent / Zn(Cu/Ag) / aq. methanol / 5 h / 40 °C View Scheme

1: 2,2-dimethoxypropane; TMSCl / 20 °C 2: MCPBA; NaHCO3 / CH2Cl2 / 0 - 20 °C 3: H2O / (R,R)-(salen)Co(III)(OAc) / diethyl ether / 0 - 20 °C 4: imidazole; Et3N / dimethylformamide / 0 - 20 °C 5: 100 percent / Et3N / Lindlar catalyst / hexane / 0 - 20 °C 6: 54 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 7: 50 percent / CrCl2 / tetrahydrofuran / 0 °C 8: CuI; NPrNH2 / Pd(PPh3)4 / benzene / 20 °C 9: pyridinium p-toluenesulfonate / methanol / 20 °C 10: aq. HCl / methanol / 0.25 h / 20 °C 11: 70 percent / Zn(Cu/Ag) / aq. methanol / 5 h / 40 °C View Scheme

1: H2O / (R,R)-(salen)Co(III)(OAc) / diethyl ether / 0 - 20 °C 2: imidazole; Et3N / dimethylformamide / 0 - 20 °C 3: 100 percent / Et3N / Lindlar catalyst / hexane / 0 - 20 °C 4: 54 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 5: 50 percent / CrCl2 / tetrahydrofuran / 0 °C 6: CuI; NPrNH2 / Pd(PPh3)4 / benzene / 20 °C 7: pyridinium p-toluenesulfonate / methanol / 20 °C 8: aq. HCl / methanol / 0.25 h / 20 °C 9: 70 percent / Zn(Cu/Ag) / aq. methanol / 5 h / 40 °C View Scheme

1: MCPBA; NaHCO3 / CH2Cl2 / 0 - 20 °C 2: H2O / (R,R)-(salen)Co(III)(OAc) / diethyl ether / 0 - 20 °C 3: imidazole; Et3N / dimethylformamide / 0 - 20 °C 4: 100 percent / Et3N / Lindlar catalyst / hexane / 0 - 20 °C 5: 54 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 6: 50 percent / CrCl2 / tetrahydrofuran / 0 °C 7: CuI; NPrNH2 / Pd(PPh3)4 / benzene / 20 °C 8: pyridinium p-toluenesulfonate / methanol / 20 °C 9: aq. HCl / methanol / 0.25 h / 20 °C 10: 70 percent / Zn(Cu/Ag) / aq. methanol / 5 h / 40 °C View Scheme

1: imidazole; Et3N / dimethylformamide / 0 - 20 °C 2: 100 percent / Et3N / Lindlar catalyst / hexane / 0 - 20 °C 3: 54 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 4: 50 percent / CrCl2 / tetrahydrofuran / 0 °C 5: CuI; NPrNH2 / Pd(PPh3)4 / benzene / 20 °C 6: pyridinium p-toluenesulfonate / methanol / 20 °C 7: aq. HCl / methanol / 0.25 h / 20 °C 8: 70 percent / Zn(Cu/Ag) / aq. methanol / 5 h / 40 °C View Scheme