1: 1.) BBN, 2.) Cs2CO3, AsPh3, Pd(dppf)2Cl2, H2O / 1.) THF, 25 deg C, 2 h, 2.) THF, DMF, 2 h 2: HCl / methanol / 3.5 h / 25 °C 3: 81 percent / <RuCl2((R)-BINAP)>2<NEt3>, H2, HCl / methanol / 14 h / 25 °C / 62057.8 Torr 4: 2,6-lutidine / CH2Cl2 / -78 - 20 °C 5: HCl / tetrahydrofuran; methanol / 0 °C 6: 1.) Et3N, 2,4,6-trichlorobenzoyl chloride, 2.) DMAP / 1.) THF, RT, 15 min, 2.) THF, toluene, 0.5 h 7: 82 percent / SmI2, NiI2 / tetrahydrofuran / 2 h / -78 °C 8: 91 percent / HF*pyridine / tetrahydrofuran / 5 h / 0 °C 9: 80 percent / DMDO / CH2Cl2 View Scheme

1: 1.) BBN, 2.) Cs2CO3, AsPh3, Pd(dppf)2Cl2, H2O / 1.) THF, 25 deg C, 2 h, 2.) THF, DMF, 2 h 2: HCl / methanol / 3.5 h / 25 °C 3: 81 percent / <RuCl2((R)-BINAP)>2<NEt3>, H2, HCl / methanol / 14 h / 25 °C / 62057.8 Torr 4: 2,6-lutidine / CH2Cl2 / -78 - 20 °C 5: HCl / tetrahydrofuran; methanol / 0 °C 6: 1.) Et3N, 2,4,6-trichlorobenzoyl chloride, 2.) DMAP / 1.) THF, RT, 15 min, 2.) THF, toluene, 0.5 h 7: 82 percent / SmI2, NiI2 / tetrahydrofuran / 2 h / -78 °C 8: 91 percent / HF*pyridine / tetrahydrofuran / 5 h / 0 °C View Scheme