1: 95 percent / CeCl3*6H2O, NaBH4 / methanol / 0 °C / 5 to 10 min 2: 1a) MS 3 Angstroem, diisopropyl (-)-tartrate, 1b) Ti(O-i-Pr)4, 2) cumene hydroperoxide / 1a) CH2Cl2, r.t., 1b) -5 deg C, 20 min, 2a) -5 deg C, 8 h, 2b) 4 deg C, overnight 3: 51 percent / Ti(O-i-Pr)4 / benzene / 0.33 h 4: 98 percent / camphorsulfonic acid / CH2Cl2 / 5 h 5: 90 percent / LiAlH4 / diethyl ether / 1 h / Heating 6: 67 percent / pyridinium dichromate / dimethylformamide / 30 h / Ambient temperature 7: 99 percent / diethyl ether 8: 93 percent / Ti(OEt)4 / 60 h / 100 °C 9: 1) O3, 2) Me2S / 1) CH2Cl2, -78 deg C, 45 min, 2) to r.t., 7 h 10: 67 percent / NaIO4, 2 percent RuCl3*3H2O / acetonitrile; CCl4 / 0.33 h / Ambient temperature; phosphate buffer, pH 7 11: 96 percent / HOAc / H2O / 8 h / 75 °C 12: 74 percent / 2-chloro-1-methylpyridinium iodide, 4-(dimethylamino)pyridine / acetonitrile / a) 0 deg C, 3 h, b) r.t., 10 h 13: 91 percent / (i-Pr)2NEt / tetrahydrofuran / 15 h / 50 °C 14: 1) N-isopropylcyclohexylamine, n-BuLi / 1) THF, hexane, -60 to -50 deg C, 45 min, 2a) -60 deg C, 45 min, 2b) to -20 deg C, 10 min 15: Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 6 h 16: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 15 h / 4 °C 17: 90 percent / 3 M aq. HCl / tetrahydrofuran / a) r.t., 1 h, b) 35 deg C, 10 h 18: 60 percent / RuCl3*3H2O, 30 percent aq. H2O2 / tetrahydrofuran / a) 0 deg C, 0.5 h, b) r.t., 2 h 19: 91 percent / camphorsulfonic acid / CHCl3 / 12 h / Ambient temperature View Scheme

Multi-step reaction with 2 steps 1: 95 percent / CeCl3*6H2O, NaBH4 / methanol / 0 °C / 5 to 10 min2: 1a) MS 3 Angstroem, diisopropyl (-)-tartrate, 1b) Ti(O-i-Pr)4, 2) cumene hydroperoxide / 1a) CH2Cl2, r.t., 1b) -5 deg C, 20 min, 2a) -5 deg C, 8 h, 2b) 4 deg C, overnight  

Multi-step reaction with 3 steps 1: 95 percent / CeCl3*6H2O, NaBH4 / methanol / 0 °C / 5 to 10 min2: 1a) MS 3 Angstroem, diisopropyl (-)-tartrate, 1b) Ti(O-i-Pr)4, 2) cumene hydroperoxide / 1a) CH2Cl2, r.t., 1b) -5 deg C, 20 min, 2a) -5 deg C, 8 h, 2b) 4 deg C, overnight3: 51 percent / Ti(O-i-Pr)4 / benzene / 0.33 h  

Multi-step reaction with 4 steps 1: 95 percent / CeCl3*6H2O, NaBH4 / methanol / 0 °C / 5 to 10 min2: 1a) MS 3 Angstroem, diisopropyl (-)-tartrate, 1b) Ti(O-i-Pr)4, 2) cumene hydroperoxide / 1a) CH2Cl2, r.t., 1b) -5 deg C, 20 min, 2a) -5 deg C, 8 h, 2b) 4 deg C, overnight3: 51 percent / Ti(O-i-Pr)4 / benzene / 0.33 h4: 98 percent / camphorsulfonic acid / CH2Cl2 / 5 h  

Multi-step reaction with 5 steps 1: 95 percent / CeCl3*6H2O, NaBH4 / methanol / 0 °C / 5 to 10 min2: 1a) MS 3 Angstroem, diisopropyl (-)-tartrate, 1b) Ti(O-i-Pr)4, 2) cumene hydroperoxide / 1a) CH2Cl2, r.t., 1b) -5 deg C, 20 min, 2a) -5 deg C, 8 h, 2b) 4 deg C, overnight3: 51 percent / Ti(O-i-Pr)4 / benzene / 0.33 h4: 98 percent / camphorsulfonic acid / CH2Cl2 / 5 h5: 90 percent / LiAlH4 / diethyl ether / 1 h / Heating  

Multi-step reaction with 10 steps 1: 95 percent / CeCl3*6H2O, NaBH4 / methanol / 0 °C / 5 to 10 min2: 1a) MS 3 Angstroem, diisopropyl (-)-tartrate, 1b) Ti(O-i-Pr)4, 2) cumene hydroperoxide / 1a) CH2Cl2, r.t., 1b) -5 deg C, 20 min, 2a) -5 deg C, 8 h, 2b) 4 deg C, overnight3: 51 percent / Ti(O-i-Pr)4 / benzene / 0.33 h4: 98 percent / camphorsulfonic acid / CH2Cl2 / 5 h5: 90 percent / LiAlH4 / diethyl ether / 1 h / Heating6: 67 percent / pyridinium dichromate / dimethylformamide / 30 h / Ambient temperature7: 99 percent / diethyl ether8: 93 percent / Ti(OEt)4 / 60 h / 100 °C9: 1) O3, 2) Me2S / 1) CH2Cl2, -78 deg C, 45 min, 2) to r.t., 7 h10: 67 percent / NaIO4, 2 percent RuCl3*3H2O / acetonitrile; CCl4 / 0.33 h / Ambient temperature; phosphate buffer, pH 7  

Multi-step reaction with 12 steps 1: 95 percent / CeCl3*6H2O, NaBH4 / methanol / 0 °C / 5 to 10 min2: 1a) MS 3 Angstroem, diisopropyl (-)-tartrate, 1b) Ti(O-i-Pr)4, 2) cumene hydroperoxide / 1a) CH2Cl2, r.t., 1b) -5 deg C, 20 min, 2a) -5 deg C, 8 h, 2b) 4 deg C, overnight3: 51 percent / Ti(O-i-Pr)4 / benzene / 0.33 h4: 98 percent / camphorsulfonic acid / CH2Cl2 / 5 h5: 90 percent / LiAlH4 / diethyl ether / 1 h / Heating6: 67 percent / pyridinium dichromate / dimethylformamide / 30 h / Ambient temperature7: 99 percent / diethyl ether8: 93 percent / Ti(OEt)4 / 60 h / 100 °C9: 1) O3, 2) Me2S / 1) CH2Cl2, -78 deg C, 45 min, 2) to r.t., 7 h10: 67 percent / NaIO4, 2 percent RuCl3*3H2O / acetonitrile; CCl4 / 0.33 h / Ambient temperature; phosphate buffer, pH 711: 96 percent / HOAc / H2O / 8 h / 75 °C12: 74 percent / 2-chloro-1-methylpyridinium iodide, 4-(dimethylamino)pyridine / acetonitrile / a) 0 deg C, 3 h, b) r.t., 10 h  

Multi-step reaction with 13 steps 1: 95 percent / CeCl3*6H2O, NaBH4 / methanol / 0 °C / 5 to 10 min2: 1a) MS 3 Angstroem, diisopropyl (-)-tartrate, 1b) Ti(O-i-Pr)4, 2) cumene hydroperoxide / 1a) CH2Cl2, r.t., 1b) -5 deg C, 20 min, 2a) -5 deg C, 8 h, 2b) 4 deg C, overnight3: 51 percent / Ti(O-i-Pr)4 / benzene / 0.33 h4: 98 percent / camphorsulfonic acid / CH2Cl2 / 5 h5: 90 percent / LiAlH4 / diethyl ether / 1 h / Heating6: 67 percent / pyridinium dichromate / dimethylformamide / 30 h / Ambient temperature7: 99 percent / diethyl ether8: 93 percent / Ti(OEt)4 / 60 h / 100 °C9: 1) O3, 2) Me2S / 1) CH2Cl2, -78 deg C, 45 min, 2) to r.t., 7 h10: 67 percent / NaIO4, 2 percent RuCl3*3H2O / acetonitrile; CCl4 / 0.33 h / Ambient temperature; phosphate buffer, pH 711: 96 percent / HOAc / H2O / 8 h / 75 °C12: 74 percent / 2-chloro-1-methylpyridinium iodide, 4-(dimethylamino)pyridine / acetonitrile / a) 0 deg C, 3 h, b) r.t., 10 h13: 91 percent / (i-Pr)2NEt / tetrahydrofuran / 15 h / 50 °C