1: 1.) n-Bu3SnLi, 2.) I2 / 2.) Et2O 3: n-PrNH2 / Pd(PPh3)4, CuI 4: 1.) (Sia)2BH, AcOH; 2.) H2O2, NaOH / 1.) THF 5: n-Bu4NF 6: 79 percent / LiOH View Scheme

1: 74 percent / PPh3, diethyl azadicarboxylate / tetrahydrofuran 2: 61 percent / 1N NaOH / methanol / 1 h / 0 °C 3: 1) Bu3SnLi, 2) I2 / 1) THF, 0 deg C, 3h, 2) Et2O 4: 97 percent / imidazole / dimethylformamide 5: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h 6: 55 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature View Scheme