1: 1.) butyllithium / 1.) THF, -23 deg C, 60 min, 2.) THF, a) -23 deg C, 4 h, b) RT, 14 h 2: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h 3: 94.4 percent / H2 / 10percent Pd/C / methanol; ethyl acetate / Ambient temperature View Scheme

1: 1.) butyllithium / 1.) THF, -23 deg C, 60 min, 2.) THF, a) -23 deg C, 4 h, b) RT, 14 h 2: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h 3: 94.4 percent / H2 / 10percent Pd/C / methanol; ethyl acetate / Ambient temperature View Scheme

1: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h 2: 94.4 percent / H2 / 10percent Pd/C / methanol; ethyl acetate / Ambient temperature View Scheme

1: 8.2 g / ethanol / Irradiation 2: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h 3: 94.4 percent / H2 / 10percent Pd/C / methanol; ethyl acetate / Ambient temperature View Scheme

1: 1.) potassium tert-butoxide / 1.) THF, RT, 10 min, 2.) 0 deg C, 30 min 2: H2 / 10percent Pd/C / methanol / Ambient temperature View Scheme

1: With quinoline; hydrogen in hexane; toluene T=20°C; P=760.051 Torr; 1 h; 2: With tetrabutyl ammonium fluoride; water in ethyl acetate T=20°C; 0.25 h; stereoselective reaction;

1.1: methanol; potassium acetate / 0.25 h / Reflux 2.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 12 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 3.2: -78 - 20 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride; water / ethyl acetate / 0.17 h / 20 °C 5.1: 10 palladium on activated charcoal; hydrogen; ethylenediamine / methanol / 1 h / 20 °C / 760.05 Torr View Scheme

1.1: methanol; potassium acetate / 0.25 h / Reflux 2.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 12 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 3.2: -78 - 20 °C / Inert atmosphere 4.1: quinoline; hydrogen / hexane; toluene / 1 h / 20 °C / 760.05 Torr 4.2: 0.25 h / 20 °C View Scheme

1.1: methanesulfonic acid; phosphorous pentoxide / 4 h / 40 °C 2.1: methanol; potassium acetate / 0.25 h / Reflux 3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 12 h / 20 °C 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 4.2: -78 - 20 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride; water / ethyl acetate / 0.17 h / 20 °C 6.1: 10 palladium on activated charcoal; hydrogen; ethylenediamine / methanol / 1 h / 20 °C / 760.05 Torr View Scheme

1.1: methanesulfonic acid; phosphorous pentoxide / 4 h / 40 °C 2.1: methanol; potassium acetate / 0.25 h / Reflux 3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 12 h / 20 °C 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 4.2: -78 - 20 °C / Inert atmosphere 5.1: quinoline; hydrogen / hexane; toluene / 1 h / 20 °C / 760.05 Torr 5.2: 0.25 h / 20 °C View Scheme