ozone; triethylamine 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, from -78 deg C to RT; Yield given. Multistep reaction;

1: 1.) potassium t-butoxide / 1.) THF, -20 deg C 2h; 2.) THF, -13 deg C, rt 12 h 2: 80 percent / p-toluenesulfonic acid / methanol / 1.) rt 40 min; 2.) 50 deg C 2.5 h 3: pyridine / 1.) 0 deg C; 2.) rt 12 h View Scheme

1: 1.) NaNH2, HMPA / 1.) THF, RT, 90 min, 2.) THF, from -78 deg C to RT, 5 h 2: 89 percent / CBr4, Ph3P / CH2Cl2 / Ambient temperature 3: 1.) n-BuLi / 1.) hexane, THF, -10 deg C, 30 min, 2.) hexane, THF, HMPA, -10 deg C, 3 h 4: 57 percent / p-toluenesulfonic acid / methanol / 4 h / 60 °C View Scheme

1: 1.) NaNH2, HMPA / 1.) THF, RT, 90 min, 2.) THF, from -78 deg C to RT, 5 h 2: 89 percent / CBr4, Ph3P / CH2Cl2 / Ambient temperature 3: 1.) n-BuLi / 1.) hexane, THF, -10 deg C, 30 min, 2.) hexane, THF, HMPA, -10 deg C, 3 h View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, RT, 15 min, 2.) THF, hexane, RT, 18 h 2: 91 percent / H2 / 10percent Pd/C / ethanol / 12 h 3: 94 percent / p-toluenesulfonic acid, H2O / tetrahydrofuran / 18 h / Ambient temperature 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, 0 deg C, 20 min 5: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, 1 h 6: 91 percent / ethanethiol, NaH / dimethylformamide / 3 h / Heating 7: 62.4 percent / N-bromosuccinimide (NBS) / CCl4 / 4 h / Ambient temperature 8: 31 percent / salcomine, O2 / dimethylformamide / 20 h / Ambient temperature 9: 97 percent / Pd(PPh3)4, 2 N aq. Na2CO3 / tetrahydrofuran / 0.17 h / 90 °C 10: 80 mg / HClO4 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, RT, 15 min, 2.) THF, hexane, RT, 18 h 2: 91 percent / H2 / 10percent Pd/C / ethanol / 12 h 3: 94 percent / p-toluenesulfonic acid, H2O / tetrahydrofuran / 18 h / Ambient temperature 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, 0 deg C, 20 min 5: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, 1 h 6: 91 percent / ethanethiol, NaH / dimethylformamide / 3 h / Heating 7: 62.7 percent / salcomine, O2 / dimethylformamide / 14 h View Scheme

1: 1.) NaNH2, HMPA / 1.) THF, RT, 90 min, 2.) THF, from -78 deg C to RT, 5 h 2: 89 percent / CBr4, Ph3P / CH2Cl2 / Ambient temperature 3: 1.) n-BuLi / 1.) hexane, THF, -10 deg C, 30 min, 2.) hexane, THF, HMPA, -10 deg C, 3 h 4: 57 percent / p-toluenesulfonic acid / methanol / 4 h / 60 °C 5: 58 percent / LAH / bis-(2-methoxy-ethyl) ether / 48 h / Heating 6: 81 percent / pyridine / CH2Cl2 / 5 h / Ambient temperature View Scheme