sodium

1: 80 percent / DMAP; NEt3 / CH2Cl2 / 20 °C 2: 71 percent / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C 3: 97 percent / PPy 4: 86 percent / TBAF / tetrahydrofuran / 20 °C 5: 52 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C 6: Ph3SnH; AIBN / benzene / 2 h / Heating View Scheme

1: 80 percent / DMAP; Et3N / CH2Cl2 / 20 °C 2: 94 percent / NaBH4 / methanol / 0.5 h / 20 °C 3: 96 percent / PPTs / CH2Cl2 / 20 °C 4: 98 percent / TBAF / tetrahydrofuran / 2 h / 20 °C 5: 100 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C 6: 96 percent / PPTs / ethanol / 4 h / 55 - 60 °C 7: 52 percent / DMAP / CH2Cl2 / 24 h / 20 °C 8: 60 percent / Ph3SnH; AIBN / benzene; acetonitrile / 2 h / Heating View Scheme

1: With oxalyl dichloride; dimethyl sulfoxide in dichloromethane T=-78°C; Swern Oxidation; 3 h; Inert atmosphere; 2: With triethylamine in dichloromethane T=-78 - 20°C; Swern Oxidation; 3.5 h; Inert atmosphere;