Yield given. Multistep reaction;

Multi-step reaction with 7 steps 1: 91 percent / (i-Pr)2NEt / tetrahydrofuran / 15 h / 50 °C2: 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 min3: Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 6 h4: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 15 h / 4 °C5: 90 percent / 3 M aq. HCl / tetrahydrofuran / a) r.t., 1 h, b) 35 deg C, 10 h6: 60 percent / RuCl3*3H2O, 30 percent aq. H2O2 / tetrahydrofuran / a) 0 deg C, 0.5 h, b) r.t., 2 h7: 91 percent / camphorsulfonic acid / CHCl3 / 12 h / Ambient temperature  

Multi-step reaction with 2 steps 1: 60 percent / RuCl3*3H2O, 30 percent aq. H2O2 / tetrahydrofuran / a) 0 deg C, 0.5 h, b) r.t., 2 h2: 91 percent / camphorsulfonic acid / CHCl3 / 12 h / Ambient temperature  

Multi-step reaction with 6 steps 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 min2: Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 6 h3: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 15 h / 4 °C4: 90 percent / 3 M aq. HCl / tetrahydrofuran / a) r.t., 1 h, b) 35 deg C, 10 h5: 60 percent / RuCl3*3H2O, 30 percent aq. H2O2 / tetrahydrofuran / a) 0 deg C, 0.5 h, b) r.t., 2 h6: 91 percent / camphorsulfonic acid / CHCl3 / 12 h / Ambient temperature  

Multi-step reaction with 9 steps 1: 96 percent / HOAc / H2O / 8 h / 75 °C2: 74 percent / 2-chloro-1-methylpyridinium iodide, 4-(dimethylamino)pyridine / acetonitrile / a) 0 deg C, 3 h, b) r.t., 10 h3: 91 percent / (i-Pr)2NEt / tetrahydrofuran / 15 h / 50 °C4: 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 min5: Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 6 h6: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 15 h / 4 °C7: 90 percent / 3 M aq. HCl / tetrahydrofuran / a) r.t., 1 h, b) 35 deg C, 10 h8: 60 percent / RuCl3*3H2O, 30 percent aq. H2O2 / tetrahydrofuran / a) 0 deg C, 0.5 h, b) r.t., 2 h9: 91 percent / camphorsulfonic acid / CHCl3 / 12 h / Ambient temperature  

Multi-step reaction with 3 steps 1: 90 percent / 3 M aq. HCl / tetrahydrofuran / a) r.t., 1 h, b) 35 deg C, 10 h2: 60 percent / RuCl3*3H2O, 30 percent aq. H2O2 / tetrahydrofuran / a) 0 deg C, 0.5 h, b) r.t., 2 h3: 91 percent / camphorsulfonic acid / CHCl3 / 12 h / Ambient temperature