1: 52.3 g / 1.) CuCN, LiCl / 1.) THF, 0 deg C, 2.) THF-Et2O, 0 deg C 2: 1.) Li, 2.) ZnBr2, 3.) Pd(PPh3)4 / 1.) Et2O, 2.) Et2O-THF, -20 deg C, 3.) RT 3: 95 percent / FeCl3 / diethyl ether / Ambient temperature 4: 87 percent / 2N KOH / methanol 5: 64 percent / pyridine 6: 92 percent / NaI / acetone 7: 86 percent / 1.) n-BuLi, 2.) HMPT / 1.) THF-hexane, 0 deg C, 1 h; -> RT, 1 h, 2.) 0 deg C -> RT; then RT, overnight 8: 86 percent / p-TsOH 9: 99.3 percent / sodium bis(methoxyethoxy)aluminum hydride / diethyl ether; toluene / 48 h / Ambient temperature View Scheme

1: 98 percent / diethyl ether / 5 h / 20 °C 2: 75 percent / oxalyl chloride; DMSO / CH2Cl2 / 3 h / -60 °C 3: 39 percent / pyrrolidine / methanol / 20 °C View Scheme

in tetrahydrofuran T=-30 - 20°C; 8 h;

1: 65 percent / (Ph3P)4Ni / benzene; diethyl ether / 2 h 2: 98 percent / perchloric acid / 3 h 3: 1.) (Ph3P)4Pd, 2.) copper iodide / 1.) C6H6, 40 min, 2.) 48 h, room temperature 4: diisoamylborane / 89 h View Scheme