1: NaIO4 / acetone; H2O / 0.5 h / 20 °C 2: p-TSA / benzene / 6 h / Heating 3: 95 percent / Pd-CaCO3 / methanol / 24 h / 20 °C 4: DBU / toluene / 24 h / Heating 5: NaBH4 / ethanol / 2 h / Heating 6: 74 percent / Et3N; DMAP / 4 h / 0 - 20 °C 7: 78 percent / Na2S / dimethylformamide / 2 h / 100 °C 8: 82 percent / aq. HCl / acetic acid / 24 h / 20 °C 9: 89 percent / CH2Cl2 / 12 h / 20 °C 10: 97 percent / aq. NaOH / methanol / 12 h / 0 °C 11: 96 percent / H2 / 10percent Pd/C / 8 h / 2280.15 Torr 12: 80 percent / 48percent HBr / 2 h / Heating View Scheme