DNAD; triphenylphosphine in dichloromethane T=0 - 20°C; Mitsunobu reaction; 2.5 h; Inert atmosphere;

1: 70 percent / CuBr, NaOMe / 24 h / 70 °C 2: NaOH / methanol; H2O / 3 h / Ambient temperature 3: ethyl acetate / 6 h / 65 °C 4: 89 percent / NaBH4, BF3*Et2O / tetrahydrofuran / 16 h / 25 °C 5: 61 percent / succinimide, PPh3 / tetrahydrofuran / 3.5 h / 0 °C View Scheme

1: 89 percent / NaBH4, BF3*Et2O / tetrahydrofuran / 16 h / 25 °C 2: 61 percent / succinimide, PPh3 / tetrahydrofuran / 3.5 h / 0 °C View Scheme

1: ethyl acetate / 6 h / 65 °C 2: 89 percent / NaBH4, BF3*Et2O / tetrahydrofuran / 16 h / 25 °C 3: 61 percent / succinimide, PPh3 / tetrahydrofuran / 3.5 h / 0 °C View Scheme

1: NaOH / methanol; H2O / 3 h / Ambient temperature 2: ethyl acetate / 6 h / 65 °C 3: 89 percent / NaBH4, BF3*Et2O / tetrahydrofuran / 16 h / 25 °C 4: 61 percent / succinimide, PPh3 / tetrahydrofuran / 3.5 h / 0 °C View Scheme