1: 99 percent / K2CO3 / dimethylformamide; H2O / 24 h / Ambient temperature 2: 73 percent / Ti(O-i-Pr)4, KHMDS / tetrahydrofuran; toluene / 2 h / -70 °C 3: 95 percent / H2 / Pd/C / methanol / 3 h / 760 Torr / Ambient temperature 4: 100 percent / Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C 5: 85 percent / DMAP / pyridine / 1.) 0 deg C, 30 min, 2.) room temp., 24 h 6: 87 percent / NaBH4 / dimethylsulfoxide / 16 h / 45 °C 7: 92 percent / H2 / Pd/C / methanol / 18 h / 760 Torr / Ambient temperature 8: aq. NaHCO3, NaOCl, KBr, TEMPO / acetone / 2 h / 0 °C View Scheme

1: 99 percent / K2CO3 / H2O; dimethylformamide / 24 h / Ambient temperature 2: 1.) Ti(Oi-Pr)4, 2.) KHMDS / 1.) THF, -78 deg C, 10 min, 2.) -70 deg C, 2 h 3: 89 percent / H2 / 10percent Pd/C / methanol / 3102.9 Torr / Ambient temperature 4: 96 percent / 6percent Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C View Scheme