1: 1.) Mg, 2.) Li2CuCl4 / 1.) THF, -10 deg, 30 min, 2.) THF, -10 deg C, 3 h 2: 61 percent / pyridinium p-toluenosulphonate / methanol / 6 h / 55 °C 3: 90 percent / H2, quinoline / Lindlar's catalyst / hexane 4: 80 percent / pyridine / CH2Cl2 / 5 h / Ambient temperature View Scheme

1: 1.) Mg, 2.) Li2CuCl4 / 1.) THF, -10 deg, 30 min, 2.) THF, -10 deg C, 3 h 2: 61 percent / pyridinium p-toluenosulphonate / methanol / 6 h / 55 °C View Scheme

dilithium tetrachlorocuprate; magnesium 1.) THF, -10 deg, 30 min, 2.) THF, -10 deg C, 3 h; Yield given. Multistep reaction;

1: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight 2: 1.) ammonium cerium(IV) nitrate, 2.) HClO4 / 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h View Scheme

1: 1.) LDA, 2.) SiO2 / 1.) hexane, THF, HMPTA, 0 deg C, 45 min, 2.) hexane, THF, HMPTA. 0-25 deg C 2: 98 percent / LiAlH4 / diethyl ether / 0.17 h / 0 °C 3: 100 percent / ZnBr2, Me3SiBr / CH2Cl2 / 0.25 h / -20 °C 4: 89 percent / dibenzo-18-crown-6 (DB-18-C-6) / acetonitrile / 15 h / 80 °C View Scheme