1: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 2: 84 percent / O3 / CH2Cl2 / -78 °C 3: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 4: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 5: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 2: 84 percent / O3 / CH2Cl2 / -78 °C 3: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT View Scheme

1: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 2: 84 percent / O3 / CH2Cl2 / -78 °C View Scheme

1: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 2: 84 percent / O3 / CH2Cl2 / -78 °C 3: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 4: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C View Scheme