pyridinium chlorochromate in dichloromethane T=20°C; 2 h;

1: KOH, PEG 400 / 0.5 h / 150 - 200 °C 2: p-TSA / 12 h / Ambient temperature 3: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 4: 84 percent / O3 / CH2Cl2 / -78 °C 5: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 6: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 7: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 97 percent / Br2 / CCl4 / 1.5 h 2: KOH, PEG 400 / 0.5 h / 150 - 200 °C 3: p-TSA / 12 h / Ambient temperature 4: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 5: 84 percent / O3 / CH2Cl2 / -78 °C 6: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 7: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 8: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: p-TSA / 12 h / Ambient temperature 2: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 3: 84 percent / O3 / CH2Cl2 / -78 °C 4: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 5: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 6: 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 4: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 5: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: LiNH2 / liquid ammonia 2: p-TsOH / methanol 3: 86 percent / H2 / P2Ni 4: 70 percent / PCC View Scheme

1: 85 percent / p-TsOH / CH2Cl2 / Ambient temperature 2: LiNH2 / liquid ammonia 3: p-TsOH / methanol 4: 86 percent / H2 / P2Ni 5: 70 percent / PCC View Scheme

1: p-TsOH / methanol 2: 86 percent / H2 / P2Ni 3: 70 percent / PCC View Scheme

1: 88 percent / H2 / Ni-P2 2: 94 percent / PCC View Scheme

1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C 2: 66.64 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / 20 °C View Scheme