salcomine; oxygen in N,N-dimethyl-formamide 14 h;

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: 62.7 percent / salcomine, O2 / dimethylformamide / 14 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: 62.7 percent / salcomine, O2 / dimethylformamide / 14 h View Scheme

1: 95 percent / Amberlist15 / CH2Cl2 / 6 h / Ambient temperature 2: 1.) O3, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, from -78 deg C to RT 3: 1.) n-BuLi / 1.) THF, hexane, RT, 15 min, 2.) THF, hexane, RT, 18 h 4: 91 percent / H2 / 10percent Pd/C / ethanol / 12 h 5: 94 percent / p-toluenesulfonic acid, H2O / tetrahydrofuran / 18 h / Ambient temperature 6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, 0 deg C, 20 min 7: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, 1 h 8: 91 percent / ethanethiol, NaH / dimethylformamide / 3 h / Heating 9: 62.7 percent / salcomine, O2 / dimethylformamide / 14 h 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: 62.7 percent / salcomine, O2 / dimethylformamide / 14 h View Scheme

1: 91 percent / ethanethiol, NaH / dimethylformamide / 3 h / Heating 2: 62.7 percent / salcomine, O2 / dimethylformamide / 14 h View Scheme

1: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, 1 h 2: 91 percent / ethanethiol, NaH / dimethylformamide / 3 h / Heating 3: 62.7 percent / salcomine, O2 / dimethylformamide / 14 h View Scheme

1: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, 0 deg C, 20 min 2: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, 1 h 3: 91 percent / ethanethiol, NaH / dimethylformamide / 3 h / Heating 4: 62.7 percent / salcomine, O2 / dimethylformamide / 14 h View Scheme

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