1: 46 percent / 1.) diisopropylamine, n-butyllithium / 1.) THF, hexane, -78 deg C, 15 min, 2.) -78 deg, 20 min, 3.) THF, -78 deg C, 10 min (adding), then same temp, 2 h 2: 91 percent / H2 / 5percent Pd-C / ethanol / 1.6 h / Ambient temperature 3: 1.) potassium t-butoxide / 1.) benzene, 30 deg C (adding), then 70 deg C, 4 h, 2.) HMPA-H2O, 175 deg C, 15 min 4: 72 percent / H2 / 5percent Pd-C / ethyl acetate / 96 h / Ambient temperature 5: p-toluenesulfonic acid / CH2Cl2; tetrahydrofuran / 0.17 h / 10 °C 6: 1.) Na / 1.) DMSO, 25 deg C (prep. of reagent), 2.) DMSO, 35 deg C, 16 h 7: O.5 N HCl / tetrahydrofuran / 0.17 h / 0 °C 8: diethyl ether 9: 98 percent / SO3*pyridine complex / dimethylsulfoxide; triethylamine / 0.25 h / Ambient temperature 10: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h 11: 65percent AcOH / tetrahydrofuran / 0.75 h / 50 °C 12: 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 13: 96 percent / 5percent aq KOH / ethanol / 0.33 h / 50 °C View Scheme