1: 1.) potassium t-butoxide, 2.) NaCl / 1.) benzene, 50 deg C (adding), then 65 deg C, 1.5 h, 2.) DMSO-H2O, 120 deg C, 1.5 h 2: 77 percent / N-bromosuccinimide / dimethylsulfoxide; H2O / 15 deg C (adding), then RT, 30 min 3: 89 percent / n-Bu3SnH, azobisisobutyronitrile / benzene / 2 h / Ambient temperature; Irradiation 4: 97 percent / p-toluenesulfonic acid monohydrate / CH2Cl2 / 10 deg C (adding), then RT, 30 min 5: 72 percent / H2 / 5percent Pd-C / ethyl acetate / 96 h / Ambient temperature 6: p-toluenesulfonic acid / CH2Cl2; tetrahydrofuran / 0.17 h / 10 °C 7: 1.) Na / 1.) DMSO, 25 deg C (prep. of reagent), 2.) DMSO, 35 deg C, 16 h 8: O.5 N HCl / tetrahydrofuran / 0.17 h / 0 °C 9: diethyl ether 10: 98 percent / SO3*pyridine complex / dimethylsulfoxide; triethylamine / 0.25 h / Ambient temperature 11: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h 12: 65percent AcOH / tetrahydrofuran / 0.75 h / 50 °C 13: 83 percent / diisobutylaluminum hydride, 2,6-di-t-butyl-4-methylphenol / 1.) toluene, 5 deg C, 1 h, 2.) toluene, -78 deg C (adding), up to -10 deg C within 2.5 h, then -10 deg C, 10 min 14: 96 percent / 5percent aq KOH / ethanol / 0.33 h / 50 °C View Scheme