1: p-TSA, acetone / 6 h / Ambient temperature 2: 1.) BBN, 2.) Cs2CO3, AsPh3, Pd(dppf)2Cl2, H2O / 1.) THF, 25 deg C, 2 h, 2.) THF, DMF, 2 h 3: HCl / methanol / 3.5 h / 25 °C 4: 81 percent / <RuCl2((R)-BINAP)>2<NEt3>, H2, HCl / methanol / 14 h / 25 °C / 62057.8 Torr 5: 2,6-lutidine / CH2Cl2 / -78 - 20 °C 6: HCl / tetrahydrofuran; methanol / 0 °C 7: 1.) Et3N, 2,4,6-trichlorobenzoyl chloride, 2.) DMAP / 1.) THF, RT, 15 min, 2.) THF, toluene, 0.5 h 8: 82 percent / SmI2, NiI2 / tetrahydrofuran / 2 h / -78 °C 9: 91 percent / HF*pyridine / tetrahydrofuran / 5 h / 0 °C 10: 80 percent / DMDO / CH2Cl2 View Scheme

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

1: tetrahydrofuran / 1 h / 25 °C 2: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h 3: tetrahydrofuran / 19 h / 40 °C 4: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C 5: 70 percent / Et3N / acetonitrile / 16 h / 20 °C 6: 82 percent / p-TsOH / acetone / 22 h / 20 °C 7: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr 8: TFA / CH2Cl2 / 2 h / 20 °C 9: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 10: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 11: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C View Scheme