1: 96 percent / NaIO4; RuCl3*H2O / CCl4; acetonitrile; H2O / 6 h 2: (COCl)2 / toluene; dimethylformamide / 1 h 3: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 4: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 5: NEt3 / CH2Cl2 6: 85 percent / NaN3; 15-crown-6; DMPU View Scheme

1: 96 percent / NaIO4; RuCl3*H2O / CCl4; acetonitrile; H2O / 6 h 2: (COCl)2 / toluene; dimethylformamide / 1 h 3: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 4: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 5: NEt3 / CH2Cl2 6: 85 percent / NaN3; 15-crown-6; DMPU 7: 59 percent / 2-OH-pyridine; NEt3 8: H2; aq. HCl / Pd/C / methanol View Scheme

1: 96 percent / NaIO4; RuCl3*H2O / CCl4; acetonitrile; H2O / 6 h 2: (COCl)2 / toluene; dimethylformamide / 1 h 3: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 4: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 5: NEt3 / CH2Cl2 6: 85 percent / NaN3; 15-crown-6; DMPU 7: 59 percent / 2-OH-pyridine; NEt3 View Scheme

Multi-step reaction with 4 steps 1: 1.) LiHMDS / 1.) THF, -78 deg C, 1 h, 2.) 1 h2: 99 percent / Et3N, DMAP / tetrahydrofuran / 1 h / Ambient temperature3: 89 percent / Ph3SnH, AIBN / toluene / 3 h / 90 - 110 °C4: 99 percent / TBAF / tetrahydrofuran / 1 h / 0 °C