tetrabutyl-ammonium chloride; potassium carbonate; palladium diacetate in N,N-dimethyl-formamide T=18°C; 5 h;

manganese; zirconocene dichloride; (MeO)2Dipyr(H)2*NiCl2; lithium chloride in ethylene glycol dimethyl ether T=20°C; 5 h; Inert atmosphere; optical yield given as percent dediastereoselective reaction;

manganese; zirconocene dichloride; NiCl2(2,9-dimethyl-1,10-phenanthroline); lithium chloride in ethylene glycol dimethyl ether T=20°C; Inert atmosphere;

manganese; zirconocene dichloride; (MeO)2Phen(Me)2*NiCl2; lithium chloride in ethylene glycol dimethyl ether T=20°C; 2 h; Inert atmosphere;

bis-triphenylphosphine-palladium(II) chloride; diisobutylaluminium hydride in tetrahydrofuran 24 h; Ambient temperature;

tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=50°C; P=2280 Torr; Yield given. Yields of byproduct given;

copper(l) iodide; N-butylamine; tetrakis(triphenylphosphine) palladium(0) in benzene T=20°C; Sonogashira coupling;

manganese; zirconocene dichloride; NiCl2(2,9-dimethyl-1,10-phenanthroline); lithium chloride in ethylene glycol dimethyl ether T=20°C; Inert atmosphere;

manganese; zirconocene dichloride; (MeO)2Phen(Me)2*NiCl2; lithium chloride in ethylene glycol dimethyl ether T=20°C; 2 h; Inert atmosphere;

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