sodium iodide in acetone Iodination;

1H-imidazole; iodine; triphenylphosphine in dichloromethane 2 h; DarknessInert atmosphere;

copper(l) iodide

1: silver(l) oxide / ethyl acetate / 20 °C 2: sulfuric acid; water / tetrahydrofuran / 20 - 55 °C / |Reflux View Scheme

1.1: caesium carbonate / N,N-dimethyl-formamide / 0.67 h / |Darkness; |Inert atmosphere 1.2: 45 °C / |Inert atmosphere 2.1: potassium carbonate / methanol / 35 h / |Darkness; |Inert atmosphere 3.1: Mn(dpm)3; tert.-butylhydroperoxide; phenyl silane / isopropyl alcohol; hexane / |Inert atmosphere View Scheme

1.1: caesium carbonate / N,N-dimethyl-formamide / 0.67 h / |Darkness; |Inert atmosphere 1.2: 45 °C / |Inert atmosphere 2.1: potassium carbonate / methanol / 35 h / |Darkness; |Inert atmosphere 3.1: Mn(dpm)3; tert.-butylhydroperoxide; phenyl silane / isopropyl alcohol; hexane / |Inert atmosphere 4.1: lithium aluminium tetrahydride / diethyl ether / 4 h / |Inert atmosphere View Scheme

in dimethyl sulfoxide T=0°C; Condensation; 6 h;

1.1: n-BuLi / tetrahydrofuran; hexane / 0.58 h / -78 °C 1.2: HMPA / tetrahydrofuran; hexane / -78 - 20 °C 2.1: 0.67 g / NaOH / diethyl ether; H2O / 1 h / 20 °C View Scheme

1: 90 percent / dimethylsulfoxide / 6 h / 0 °C 2: DIBAH / hexane / 23 °C View Scheme