1: oxacyclooctadecan-2-one With potassium hydroxide in ethanol 2 h; Reflux; 2: methyl iodide With sodium hydrogencarbonate in N,N-dimethyl-formamide T=0 - 20°C; Inert atmosphere;

1.1: sodium hydroxide; para-dicyanobenzene; phenanthrene / acetonitrile; water / 6 h / 20 °C / |Inert atmosphere; |UV-irradiation 2.1: potassium hydroxide / ethanol / 2 h / |Reflux 2.2: 0 - 20 °C / |Inert atmosphere View Scheme

1.1: potassium hydroxide / ethanol / 2 h / |Reflux 2.1: pyridine / N,N-dimethyl-formamide / 0 - 20 °C / |Inert atmosphere 3.1: triethylamine / dichloromethane / 0 - 20 °C / |Inert atmosphere 4.1: MgBr2(Et2O) / diethyl ether / 2 h / 20 °C 5.1: sodium hydroxide; para-dicyanobenzene; phenanthrene / acetonitrile; water / 6 h / 20 °C / |Inert atmosphere; |UV-irradiation 6.1: potassium hydroxide / ethanol / 2 h / |Reflux 6.2: 0 - 20 °C / |Inert atmosphere View Scheme

1.1: pyridine / N,N-dimethyl-formamide / 0 - 20 °C / |Inert atmosphere 2.1: triethylamine / dichloromethane / 0 - 20 °C / |Inert atmosphere 3.1: MgBr2(Et2O) / diethyl ether / 2 h / 20 °C 4.1: sodium hydroxide; para-dicyanobenzene; phenanthrene / acetonitrile; water / 6 h / 20 °C / |Inert atmosphere; |UV-irradiation 5.1: potassium hydroxide / ethanol / 2 h / |Reflux 5.2: 0 - 20 °C / |Inert atmosphere View Scheme

1.1: MgBr2(Et2O) / diethyl ether / 2 h / 20 °C 2.1: sodium hydroxide; para-dicyanobenzene; phenanthrene / acetonitrile; water / 6 h / 20 °C / |Inert atmosphere; |UV-irradiation 3.1: potassium hydroxide / ethanol / 2 h / |Reflux 3.2: 0 - 20 °C / |Inert atmosphere View Scheme

1.1: triethylamine / dichloromethane / 0 - 20 °C / |Inert atmosphere 2.1: MgBr2(Et2O) / diethyl ether / 2 h / 20 °C 3.1: sodium hydroxide; para-dicyanobenzene; phenanthrene / acetonitrile; water / 6 h / 20 °C / |Inert atmosphere; |UV-irradiation 4.1: potassium hydroxide / ethanol / 2 h / |Reflux 4.2: 0 - 20 °C / |Inert atmosphere View Scheme

hydrogenchloride