trifluoroacetic acid in dichloromethane 16 h;

1.1: 82 percent / DMSO; (CF3CO)2O; Et3N / CH2Cl2 / -78 - 20 °C 2.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C 2.2: tetrahydrofuran / -78 - 20 °C 3.1: H2 / Pd/C View Scheme

1.1: NaOH / H2O / 5 h 2.1: 56 percent / NaHCO3; NaI / dimethylformamide / 20 °C 3.1: 82 percent / DMSO; (CF3CO)2O; Et3N / CH2Cl2 / -78 - 20 °C 4.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C 4.2: tetrahydrofuran / -78 - 20 °C 5.1: H2 / Pd/C View Scheme

1.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C 1.2: tetrahydrofuran / -78 - 20 °C 2.1: H2 / Pd/C View Scheme

1.1: 56 percent / NaHCO3; NaI / dimethylformamide / 20 °C 2.1: 82 percent / DMSO; (CF3CO)2O; Et3N / CH2Cl2 / -78 - 20 °C 3.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C 3.2: tetrahydrofuran / -78 - 20 °C 4.1: H2 / Pd/C View Scheme

1.1: LHMDS / tetrahydrofuran / 0.25 h / -78 °C 1.2: 56 percent / p-TsOH / tetrahydrofuran / -78 °C 2.1: H2 / Pd/C View Scheme

hydrogen; palladium on activated charcoal in water

hydrogen; palladium on activated charcoal

1: CHCl3 / 2 h / Heating 2: lead nitrate, Et3N / CHCl3 / 87 h / Ambient temperature 3: 75 percent / CH2Cl2 / 16 h / Ambient temperature 4: 1.) lithium 2,2,6,6-tetramethylpiperidide (LiTMP) / 1.) THF, -78 deg C, 30 min, 2.) THF, 2 h 5: 65 percent / LiAlH4 / tetrahydrofuran / 2 h / -40 °C 6: 87 percent / PPh3, CBr4, iPr2NEt / tetrahydrofuran / 1 h / Ambient temperature 7: 66 percent / CF3CO2H / CH2Cl2 / 16 h View Scheme

1: 75 percent / CH2Cl2 / 16 h / Ambient temperature 2: 1.) lithium 2,2,6,6-tetramethylpiperidide (LiTMP) / 1.) THF, -78 deg C, 30 min, 2.) THF, 2 h 3: 65 percent / LiAlH4 / tetrahydrofuran / 2 h / -40 °C 4: 87 percent / PPh3, CBr4, iPr2NEt / tetrahydrofuran / 1 h / Ambient temperature 5: 66 percent / CF3CO2H / CH2Cl2 / 16 h View Scheme