1.1: tetrahydrofuran / 2 h / -78 °C 2.1: tetrafluoroboric acid; 3-chloro-benzenecarboperoxoic acid / dichloromethane; water / 48 h / 20 °C 2.2: 48 h / 20 °C / 3800.26 Torr 3.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C 3.2: 16 h / 20 °C View Scheme

1: 71 percent / BuLi / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) -78 deg C, 2 h 2: 97 percent / HCl / 1 h / 20 °C 3: 93 percent / tetrahydrofuran / 3 h / 20 °C 4: 1.) MCPBA / 1.) CHCl3, 0 deg C, 30 min, 2.) r.t., 24 h 5: 86 percent / H2 / 5percent Rh/Al2O3 / ethanol / 20 h / 20 °C / 4560 Torr 6: 47 percent / POCl3, pyridine / 20 °C 7: 56 percent / Na, NH3 / tetrahydrofuran / 1.5 h / -78 °C View Scheme

1: 69 percent / n-butyllithium / tetrahydrofuran / -78 °C 2: 77 percent / PhCH=Ru(PCy3)2Cl2 / CH2Cl2 / 12 h / Heating 3: 86 percent / H2 / RhCl(PPh3)3 / benzene / 20 °C / 1520 Torr 4: 92 percent / H2; acetic acid / 20 percent Pd(OH)2 on C / methanol; H2O / 12 h / 20 °C / 760 Torr 5: 96 percent / HCl / H2O / 12 h / 20 °C View Scheme

1: 69 percent / n-butyllithium / tetrahydrofuran / -78 °C 2: 77 percent / PhCH=Ru(PCy3)2Cl2 / CH2Cl2 / 12 h / Heating 3: 86 percent / H2 / RhCl(PPh3)3 / benzene / 20 °C / 1520 Torr 4: 92 percent / H2; acetic acid / 20 percent Pd(OH)2 on C / methanol; H2O / 12 h / 20 °C / 760 Torr View Scheme

1: Corey-AD-ligand-α non MeI salt; methanesulfonamide; K3[Fe(CN)6] / K2OsO4*2H2O; K2CO3 / 2-methyl-propan-2-ol; H2O / 18.5 h / 0 °C 2: 78 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 12.25 h / 0 - 20 °C 3: triphenylphosphine; diethyl azodicarboxylate / benzene / 4.25 h / 20 °C 4: 697 mg / NH4OH / methanol; H2O / 1.5 h / 20 °C 5: 87 percent / N-ethyldiisopropylamine / CH2Cl2 / 66 h / 20 °C 6: 100 percent / Bu4NF / tetrahydrofuran / 1 h / 20 °C 7: 92 percent / 4-(dimethylamino)pyridine; camphorsulfonic acid; dicyclohexylcarbodiimide / CH2Cl2 / 18.5 h / 20 °C 8: 83 percent / CF3CO2H / tetrahydrofuran; H2O / 22 h / 20 °C 9: 96 percent / 4-(dimethylamino)pyridine; camphorsulfonic acid; dicyclohexylcarbodiimide / CH2Cl2 / 14 h / 20 °C 10: 19 percent / CH3CO2H / propan-2-ol; H2O 11: triethylamine / toluene / 1 h / 20 °C 12: triethylamine; 4-(dimethylamino)pyridine / toluene / 3.5 h / 80 °C 13: 90 percent / trifluoroacetic acid / CH2Cl2 / 7.5 h / 20 °C View Scheme

1: 71 percent / BuLi / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) -78 deg C, 2 h 2: 91 percent / LiAlH4 / diethyl ether / 2.5 h / 0 °C 3: 1.) MCPBA / 1.) CHCl3, 0 deg C, 30 min, 2.) r.t., 48 h 4: 94 percent / Na, NH3 / tetrahydrofuran / 1.5 h / -78 °C 5: 70 percent / H2 / 5percent Rh/Al2O3 / ethanol / 18 h / 20 °C / 3800 Torr View Scheme