perchloric acid in dichloromethane 1 h; Ambient temperature;

silver carbonate in benzene 2 h;

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: 62.4 percent / N-bromosuccinimide (NBS) / CCl4 / 4 h / Ambient temperature 10: 31 percent / salcomine, O2 / dimethylformamide / 20 h / Ambient temperature 11: 97 percent / Pd(PPh3)4, 2 N aq. Na2CO3 / tetrahydrofuran / 0.17 h / 90 °C 12: 80 mg / HClO4 / CH2Cl2 / 2 h / Ambient temperature View Scheme

tetrabutyl ammonium fluoride; oxygen in tetrahydrofuran 0.5 h; -78 deg C to room temperature;

1: HCl gas / methanol / 1) 0 deg C, 1 h, 2) 0 deg C to rt, 1.5 h 2: K2CO3 / acetone / 12 h / Heating 3: 49 percent / Et3N, Ph3P / Pd(OAc)2 / 17 h / 80 °C 4: 95 percent / H2 / Pd/C / ethanol / 4 h 5: 86 percent / (COCl)2 / CH2Cl2; dimethylsulfoxide / 1 h / -78 °C 6: 63 percent / NaNH2 / tetrahydrofuran / 2 h / -78 °C 7: 93 percent / 48percent HBr / ethanol / 1 h 8: 91 percent / Ag2CO3 / benzene / 2 h View Scheme

1: 49 percent / Et3N, Ph3P / Pd(OAc)2 / 17 h / 80 °C 2: 95 percent / H2 / Pd/C / ethanol / 4 h 3: 86 percent / (COCl)2 / CH2Cl2; dimethylsulfoxide / 1 h / -78 °C 4: 63 percent / NaNH2 / tetrahydrofuran / 2 h / -78 °C 5: 93 percent / 48percent HBr / ethanol / 1 h 6: 91 percent / Ag2CO3 / benzene / 2 h View Scheme

1: 95 percent / H2 / Pd/C / ethanol / 4 h 2: 86 percent / (COCl)2 / CH2Cl2; dimethylsulfoxide / 1 h / -78 °C 3: 63 percent / NaNH2 / tetrahydrofuran / 2 h / -78 °C 4: 93 percent / 48percent HBr / ethanol / 1 h 5: 91 percent / Ag2CO3 / benzene / 2 h View Scheme

1: 1.) O3, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 2.) RT 2: 1.) tert-BuOK, 3.) LAH / 1.) THF, RT, 30 min, 2.) THF, 1 h, 3.) ether, RT, 4 h 3: 1.) (COCl)2, DMSO, 3.) triethylamine / 1.) CH2Cl2, -70 deg C, 5 min, 2.) 20 min, -70 deg C, 3.) 5 min at -70 deg C, -70 deg C to RT 4: 1.) n-BuLi / 1.) THF, tetramethylethylenediamine, hexane, 0 to 20 deg C; 2.) THF, RT, 1 h 5: Lithium / tetrahydrofuran; liquid ammonia / -30 °C / large excess of lithium 6: 93 percent / 48 percent HBr / ethanol / 0.25 h / 65 °C 7: 81 percent / O2 / salcomine / dimethylformamide / 3 h / Ambient temperature 8: 77 percent / 70 percent HClO4 / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 1.) tert-BuOK, 3.) LAH / 1.) THF, RT, 30 min, 2.) THF, 1 h, 3.) ether, RT, 4 h 2: 1.) (COCl)2, DMSO, 3.) triethylamine / 1.) CH2Cl2, -70 deg C, 5 min, 2.) 20 min, -70 deg C, 3.) 5 min at -70 deg C, -70 deg C to RT 3: 1.) n-BuLi / 1.) THF, tetramethylethylenediamine, hexane, 0 to 20 deg C; 2.) THF, RT, 1 h 4: Lithium / tetrahydrofuran; liquid ammonia / -30 °C / large excess of lithium 5: 93 percent / 48 percent HBr / ethanol / 0.25 h / 65 °C 6: 81 percent / O2 / salcomine / dimethylformamide / 3 h / Ambient temperature 7: 77 percent / 70 percent HClO4 / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 1.) 60 percent NaH oil dispersion / 1.) DMF, 0 deg C, 15 min, 2.) 0 deg C to RT, 3 h at RT 2: 1.) n-BuLi / 1.) THF, tetramethylethylenediamine, hexane, 0 to 20 deg C; 2.) THF, RT, 1 h 3: Lithium / tetrahydrofuran; liquid ammonia / -30 °C / large excess of lithium 4: 93 percent / 48 percent HBr / ethanol / 0.25 h / 65 °C 5: 81 percent / O2 / salcomine / dimethylformamide / 3 h / Ambient temperature 6: 77 percent / 70 percent HClO4 / CH2Cl2 / 1 h / Ambient temperature View Scheme