1: 1.) TMSCl, NaI / 1.) MeCN, 50 deg C 14 h, 2.) MeCN, 3 h 2: 98.6 percent / NaHCO3 / dimethylsulfoxide / 0.07 h / 150 °C 3: 87 percent / MeONa / dimethylformamide / 24 h / 0 - 5 °C 4: H2 / Pd/C / ethanol / 2585.74 - 10343 Torr 5: 0.56 g / NaOH / H2O View Scheme

1: 90 percent / LiALH4 / tetrahydrofuran 2: 95 percent / HBr; H2SO4 View Scheme

1.1: N,O-dimethylhydroxylamine hydrochloride; methyllithium / tetrahydrofuran / 0 - 20 °C 1.2: tetrahydrofuran / 0 - 20 °C 2.1: 2.72 g / imidazole / tetrahydrofuran / 2 h 3.1: tetrahydrofuran / 0 - 20 °C 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 7.1: pyridinium chlorochromate / dichloromethane / 4 h / 0 °C / |Inert atmosphere 8.1: tetrahydrofuran / 0 °C / |Inert atmosphere 8.2: |Inert atmosphere 9.1: pyridinium chlorochromate / dichloromethane / 4 h / 0 °C / |Inert atmosphere 10.1: MgBr2(Et2O) / diethyl ether / 2 h / 20 °C 11.1: sodium hydroxide; DCN; biphenyl / acetonitrile; water / 6 h / 20 °C / |Inert atmosphere; |UV-irradiation View Scheme

1.1: N,O-dimethylhydroxylamine hydrochloride; methyllithium / tetrahydrofuran / 0 - 20 °C 1.2: tetrahydrofuran / 0 - 20 °C 2.1: 2.72 g / imidazole / tetrahydrofuran / 2 h View Scheme

1.1: N,O-dimethylhydroxylamine hydrochloride; methyllithium / tetrahydrofuran / 0 - 20 °C 1.2: tetrahydrofuran / 0 - 20 °C 2.1: 2.72 g / imidazole / tetrahydrofuran / 2 h 3.1: tetrahydrofuran / 0 - 20 °C 4.1: 0.38 g / tetrabutylammonium fluoride / tetrahydrofuran / 15 h View Scheme

1.1: N,O-dimethylhydroxylamine hydrochloride; methyllithium / tetrahydrofuran / 0 - 20 °C 1.2: tetrahydrofuran / 0 - 20 °C 2.1: 2.72 g / imidazole / tetrahydrofuran / 2 h 3.1: tetrahydrofuran / 0 - 20 °C 4.1: 0.38 g / tetrabutylammonium fluoride / tetrahydrofuran / 15 h 5.1: 79 percent / sodium hydride / tetrahydrofuran / Heating 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: oxacyclohexadecan-2-one With methyllithium; O,N-dimethyl-hydroxylamine hydrochloride in tetrahydrofuran T=0 - 20°C; 2: methyllithium in tetrahydrofuran T=0 - 20°C;

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 7.1: triethylamine / dichloromethane / 0 - 20 °C / |Inert atmosphere 8.1: MgBr2(Et2O) / diethyl ether / 2 h / 20 °C 9.1: sodium hydroxide; para-dicyanobenzene; phenanthrene / acetonitrile; water / 6 h / 20 °C / |Inert atmosphere; |UV-irradiation View Scheme