1.1: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; triethylamine / tetrahydrofuran / 0.33 h / 20 °C / |Inert atmosphere 1.2: 15 h / 20 °C / |Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere 3.1: 1H-imidazole / tetrahydrofuran / 15 h / 0 - 20 °C / |Inert atmosphere 4.1: potassium carbonate; methanol / 2 h / 20 °C / |Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / |Inert atmosphere 5.2: 0.5 h / 20 °C / |Inert atmosphere 6.1: hydrogen; palladium 10 on activated carbon / ethyl acetate / 15001.5 Torr 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere 8.1: triethylamine / dichloromethane / 0.5 h / 0 °C / |Inert atmosphere 9.1: sodium iodide / acetone / 0.25 h / 20 °C 10.1: N,N-dimethyl-formamide / 2 h / 20 °C / |Inert atmosphere 11.1: sodium hydroxide; water / 4 h / |Reflux View Scheme

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere 2.1: 1H-imidazole / tetrahydrofuran / 15 h / 0 - 20 °C / |Inert atmosphere 3.1: potassium carbonate; methanol / 2 h / 20 °C / |Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / |Inert atmosphere 4.2: 0.5 h / 20 °C / |Inert atmosphere 5.1: hydrogen; palladium 10 on activated carbon / ethyl acetate / 15001.5 Torr 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere 7.1: triethylamine / dichloromethane / 0.5 h / 0 °C / |Inert atmosphere 8.1: sodium iodide / acetone / 0.25 h / 20 °C 9.1: N,N-dimethyl-formamide / 2 h / 20 °C / |Inert atmosphere 10.1: sodium hydroxide; water / 4 h / |Reflux View Scheme

palladium; acetic acid Hydrogenation;

1: aluminium chloride 2: acetic acid; palladium / Hydrogenation View Scheme

1: H2SO4 / Heating 2: NaOMe / toluene / 45 °C 3: NaBH4 / ethanol / 55 °C View Scheme