1: 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 2: Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 6 h 3: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 15 h / 4 °C 4: 90 percent / 3 M aq. HCl / tetrahydrofuran / a) r.t., 1 h, b) 35 deg C, 10 h 5: 60 percent / RuCl3*3H2O, 30 percent aq. H2O2 / tetrahydrofuran / a) 0 deg C, 0.5 h, b) r.t., 2 h 6: 91 percent / camphorsulfonic acid / CHCl3 / 12 h / Ambient temperature View Scheme

1: 1) O3, 2) Me2S / 1) CH2Cl2, -78 deg C, 45 min, 2) to r.t., 7 h 2: 67 percent / NaIO4, 2 percent RuCl3*3H2O / acetonitrile; CCl4 / 0.33 h / Ambient temperature; phosphate buffer, pH 7 3: 96 percent / HOAc / H2O / 8 h / 75 °C 4: 74 percent / 2-chloro-1-methylpyridinium iodide, 4-(dimethylamino)pyridine / acetonitrile / a) 0 deg C, 3 h, b) r.t., 10 h 5: 91 percent / (i-Pr)2NEt / tetrahydrofuran / 15 h / 50 °C 6: 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 7: Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 6 h 8: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 15 h / 4 °C 9: 90 percent / 3 M aq. HCl / tetrahydrofuran / a) r.t., 1 h, b) 35 deg C, 10 h 10: 60 percent / RuCl3*3H2O, 30 percent aq. H2O2 / tetrahydrofuran / a) 0 deg C, 0.5 h, b) r.t., 2 h 11: 91 percent / camphorsulfonic acid / CHCl3 / 12 h / Ambient temperature View Scheme

1: 96 percent / HOAc / H2O / 8 h / 75 °C 2: 74 percent / 2-chloro-1-methylpyridinium iodide, 4-(dimethylamino)pyridine / acetonitrile / a) 0 deg C, 3 h, b) r.t., 10 h 3: 91 percent / (i-Pr)2NEt / tetrahydrofuran / 15 h / 50 °C 4: 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 5: Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 6 h 6: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 15 h / 4 °C 7: 90 percent / 3 M aq. HCl / tetrahydrofuran / a) r.t., 1 h, b) 35 deg C, 10 h 8: 60 percent / RuCl3*3H2O, 30 percent aq. H2O2 / tetrahydrofuran / a) 0 deg C, 0.5 h, b) r.t., 2 h 9: 91 percent / camphorsulfonic acid / CHCl3 / 12 h / Ambient temperature View Scheme

1: 90 percent / 3 M aq. HCl / tetrahydrofuran / a) r.t., 1 h, b) 35 deg C, 10 h 2: 60 percent / RuCl3*3H2O, 30 percent aq. H2O2 / tetrahydrofuran / a) 0 deg C, 0.5 h, b) r.t., 2 h 3: 91 percent / camphorsulfonic acid / CHCl3 / 12 h / Ambient temperature View Scheme

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

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

1: 67 percent / NaIO4, 2 percent RuCl3*3H2O / acetonitrile; CCl4 / 0.33 h / Ambient temperature; phosphate buffer, pH 7 2: 96 percent / HOAc / H2O / 8 h / 75 °C 3: 74 percent / 2-chloro-1-methylpyridinium iodide, 4-(dimethylamino)pyridine / acetonitrile / a) 0 deg C, 3 h, b) r.t., 10 h 4: 91 percent / (i-Pr)2NEt / tetrahydrofuran / 15 h / 50 °C 5: 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 6: Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 6 h 7: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 15 h / 4 °C 8: 90 percent / 3 M aq. HCl / tetrahydrofuran / a) r.t., 1 h, b) 35 deg C, 10 h 9: 60 percent / RuCl3*3H2O, 30 percent aq. H2O2 / tetrahydrofuran / a) 0 deg C, 0.5 h, b) r.t., 2 h 10: 91 percent / camphorsulfonic acid / CHCl3 / 12 h / Ambient temperature View Scheme

Yield given. Multistep reaction;

Yield given. Multistep reaction;