sodium hydroxide in diethyl ether 0.0291667 h;

1: butadiyne With n-butyllithium in tetrahydrofuran T=-40°C; 0.5 h; 2: acrolein in tetrahydrofuran; hexane T=-40°C; 3 h;

1: 1,4-Dichloro-2-butyne With lithium amide; iron nitrate (III) in ammonia T=-50°C; 1 h; 2: acrolein in ammonia 2 h; Further stages.;

1.1: 91 percent / triethylamine; 4-(dimethylamino)pyridine / 2 h / 20 °C 2.1: Candida antarctica B lipase; Na2HPO4 buffer / 0.5 h / 20 °C / pH 7.5 / Enzymatic reaction 3.1: Bu4N(1+)*Cl(1-); K2CO3; CuI / dimethylformamide / 0.25 h / 20 °C 3.2: 69 percent / dimethylformamide / 8 h / 20 °C View Scheme

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;

copper(l) iodide; tetraethylammonium chloride; potassium carbonate in N,N-dimethyl-formamide T=20°C; Jeffery type allylation; 1 h; optical yield given as percent de;

ethylmagnesium bromide; copper dichloride 1) Et2O, 0 deg C, 30 min, reflux, 30 min, 2) Et2O, 0 deg C, reflux, 2 h; Yield givenMultistep reaction;