1: NBS / dimethylformamide / 0 °C 2: 95 percent / Pd(OAc)2; dppp; KOAc / 20 h / 110 °C 3: 82 percent / H2 / Ru-Alox / ethyl acetate / 24 h / 60 °C 4: 97 percent / TMSCl; NaI / acetonitrile / 40 °C 5: pig liver esterase / 35 °C / pH 8.0 6: 81 percent / DPPA; Et3N / CH2Cl2 / 40 °C 7: DMAP / 20 °C 8: NaH / toluene / Heating 9: pyridine / CH2Cl2 / -10 °C 10: NaN3 / acetone; H2O / 20 °C 11: H2 / Ra-Co 12: Et3N 13: HBr; AcOH View Scheme