1.1: C21H27NO; N,N-diethylaniline; benzo[1,3,2]dioxaborole / toluene / 4 h / -60 °C / |Inert atmosphere 2.1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 0.17 h / 20 °C / |Inert atmosphere 2.2: |Inert atmosphere 3.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C / |Inert atmosphere 3.2: 0.33 h / -78 °C 4.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.08 h / 0 °C / |Inert atmosphere 4.2: 0.17 h / |Inert atmosphere 5.1: ozone; triethylamine / dichloromethane / 3 h / -78 - 20 °C / |Inert atmosphere 6.1: titanium tetrachloride / dichloromethane / 0.08 h / -78 °C / |Inert atmosphere 6.2: 1 h / -78 °C / |Inert atmosphere 6.3: 3 h / -78 - 20 °C / |Inert atmosphere 7.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / |Inert atmosphere 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C / |Inert atmosphere 9.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 0.67 h / 0 °C / |Inert atmosphere 9.2: 20 °C / |Inert atmosphere 10.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C / |Inert atmosphere 11.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 °C View Scheme

N-bromosuccinmide in tetrachloromethane T=60°C; 2 h; Irradiation;

1.1: C21H27NO; N,N-diethylaniline; benzo[1,3,2]dioxaborole / toluene / 4 h / -60 °C / |Inert atmosphere 2.1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 0.17 h / 20 °C / |Inert atmosphere 2.2: |Inert atmosphere 3.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C / |Inert atmosphere 3.2: 0.33 h / -78 °C 4.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.08 h / 0 °C / |Inert atmosphere 4.2: 0.17 h / |Inert atmosphere 5.1: ozone; triethylamine / dichloromethane / 3 h / -78 - 20 °C / |Inert atmosphere 6.1: titanium tetrachloride / dichloromethane / 0.08 h / -78 °C / |Inert atmosphere 6.2: 1 h / -78 °C / |Inert atmosphere 6.3: 3 h / -78 - 20 °C / |Inert atmosphere 7.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / |Inert atmosphere 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C / |Inert atmosphere 9.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 0.67 h / 0 °C / |Inert atmosphere 9.2: 20 °C / |Inert atmosphere 10.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C / |Inert atmosphere View Scheme

1: 90 percent / acetonitrile; various solvent(s) / Irradiation; 300 nm 2: p-toluenesulfonic acid / benzene / Heating View Scheme

in acetone Irradiation300 nm;

1: With potassium hydroxide in 1,4-dioxane; water Heating / reflux; 2: With hydrogenchloride in water T=120°C; 0.25 h;

hydrogenchloride; potassium hydroxide; sodium hydrogencarbonate; methyl iodide in 1,4-dioxane; water

boron trifluoride diethyl etherate in dichloromethane T=20°C; 5 h;

boron trifluoride diethyl etherate in dichloromethane T=20°C; 5 h;

hydrogenchloride T=70°C; 3 h;