1: 81 percent / O2 / salcomine / dimethylformamide / 3 h / Ambient temperature 2: 77 percent / 70 percent HClO4 / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 93 percent / 48 percent HBr / ethanol / 0.25 h / 65 °C 2: 81 percent / O2 / salcomine / dimethylformamide / 3 h / Ambient temperature 3: 77 percent / 70 percent HClO4 / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 1.) O3, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, from -78 deg C to RT 2: 1.) n-BuLi / 1.) THF, hexane, RT, 15 min, 2.) THF, hexane, RT, 18 h 3: 91 percent / H2 / 10percent Pd/C / ethanol / 12 h 4: 94 percent / p-toluenesulfonic acid, H2O / tetrahydrofuran / 18 h / Ambient temperature 5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, 0 deg C, 20 min 6: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, 1 h 7: 91 percent / ethanethiol, NaH / dimethylformamide / 3 h / Heating 8: 62.4 percent / N-bromosuccinimide (NBS) / CCl4 / 4 h / Ambient temperature 9: 31 percent / salcomine, O2 / dimethylformamide / 20 h / Ambient temperature 10: 97 percent / Pd(PPh3)4, 2 N aq. Na2CO3 / tetrahydrofuran / 0.17 h / 90 °C 11: 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: 62.4 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: 91 percent / H2 / 10percent Pd/C / ethanol / 12 h 2: 94 percent / p-toluenesulfonic acid, H2O / tetrahydrofuran / 18 h / Ambient temperature 3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, 0 deg C, 20 min 4: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, 1 h 5: 91 percent / ethanethiol, NaH / dimethylformamide / 3 h / Heating 6: 62.4 percent / N-bromosuccinimide (NBS) / CCl4 / 4 h / Ambient temperature 7: 31 percent / salcomine, O2 / dimethylformamide / 20 h / Ambient temperature 8: 97 percent / Pd(PPh3)4, 2 N aq. Na2CO3 / tetrahydrofuran / 0.17 h / 90 °C 9: 80 mg / HClO4 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 86 percent / (COCl)2 / CH2Cl2; dimethylsulfoxide / 1 h / -78 °C 2: 63 percent / NaNH2 / tetrahydrofuran / 2 h / -78 °C 3: 93 percent / 48percent HBr / ethanol / 1 h 4: 91 percent / Ag2CO3 / benzene / 2 h View Scheme

1: 63 percent / NaNH2 / tetrahydrofuran / 2 h / -78 °C 2: 93 percent / 48percent HBr / ethanol / 1 h 3: 91 percent / Ag2CO3 / benzene / 2 h View Scheme

1: 93 percent / 48percent HBr / ethanol / 1 h 2: 91 percent / Ag2CO3 / benzene / 2 h View Scheme

1: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight 2: 1.) ammonium cerium(IV) nitrate, 2.) HClO4 / 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h View Scheme

1: mCPBA / 2 h / Ambient temperature 2: aq. KOH / ethanol / 2 h / 50 °C 3: 94 percent / NaH / dimethylformamide / 1 h / Ambient temperature 4: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight 5: 1.) ammonium cerium(IV) nitrate, 2.) HClO4 / 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h View Scheme