tetrachloromethane; triphenylphosphine T=80°C; 16 h;

1: 86 percent / H2; quinoline; KOH / Lindlar catalyst / ethanol / 16 h / atmospheric pressure 2: 81 percent / PPh3; CCl4 / 16 h / 80 °C View Scheme

methanol; barium 1.) THF, -75 deg C, 30 min, 2.) THF, 5 min; Yield given. Multistep reaction. Yields of byproduct given;

methanol; barium 1.) THF, -75 deg C, 30 min, 2.) THF, 5 min; Yield given. Multistep reaction. Yields of byproduct given;

1: (3R)-hept-1-ene-4,6-diyn-3-ol With copper(l) iodide; tetrabutyl-ammonium chloride; potassium carbonate in N,N-dimethyl-formamide T=20°C; 0.25 h; 2: (Z)-1-chlorodec-2-ene in N,N-dimethyl-formamide T=20°C; 8 h; Further stages.;

1: rac-hept-1-ene-4,6-diyn-3-ol With copper(l) iodide; tetraethylammonium chloride; potassium carbonate in N,N-dimethyl-formamide T=20°C; 0.5 h; Inert atmosphere; 2: (Z)-1-chlorodec-2-ene in N,N-dimethyl-formamide T=20°C; Jeffery type allylation; 8 h; optical yield given as percent de;

1: 7-(trimethylsilanyl)hept-1-ene-4,6-diyn-3-ol With methyllithium 2: (Z)-1-chlorodec-2-ene With copper(l) iodide