1: 69 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / 0 °C 2: 1.) dimethyl sulphide, N-chlorosuccinimide, 2.) triethylamine / 1.) toluene, ether, -20 deg C, 2 h, 2.) 30 min 3: 63 percent / benzene / 6 h / 80 °C 4: 86 percent / ethyl di-isopropylamine / CH2Cl2 / 2 h / Heating 5: 70 percent / Dowex 50W X-8 / methanol / 3 h / Ambient temperature 6: 95 percent / hydrogen / 10percent Pd-C / methanol / 4 h / 760 Torr 7: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min 8: 74 percent / butyl-lithium / hexane; tetrahydrofuran / 2 h / 0 °C 9: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 1M aq. NaOH, 30percent aq. hydrogen peroxide / 1.) THF, 4 h, reflux, 2.) 0 deg C, 30 min 10: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min, room temperature, 15 min 11: 1.) butyl-lithium, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) room temperature, 3 h 12: 98 percent / sodium hydroxide / methanol; H2O / 3 h / Ambient temperature 13: 95 percent / tetrahydrofuran / 12 h 14: 87 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 7 h / -78 °C 15: 95 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 2 h / -78 °C 16: m-chloroperoxybenzoic acid, 30percent aq. hydrogen peroxide / CDCl3 / 1.) -50 deg C, 15 min, 2.) 0 deg C, 15 min 17: 37 percent / toluene / 5 h / 100 °C 18: 98 percent / sodium hydroxide / H2O; methanol / 2 h / 0 °C 19: 98 percent / lithium di-isopropylamide / tetrahydrofuran; hexane / 2 h 20: 78 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C 21: 68 percent / pyridine, 30percent aq. hydrogen peroxide / CH2Cl2 / 12 h / Ambient temperature 22: 72 percent / sodium borohydride / ethanol / 3 h / 0 °C 23: 94 percent / pyridine, 4-dimethylaminopyridine / CH2Cl2 / 2 h / Ambient temperature 24: 19 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1.) -20 deg C, 1 h, 2.) 0 deg C, 12 h 25: 67 percent / aluminium isopropoxide / o-xylene / 5 h / 125 °C 26: 40 percent / 5percent aq. HF / acetonitrile / 3 h / Ambient temperature View Scheme

Multi-step reaction with 4 steps 1: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 15 min, 2.) -60 deg C, 15 min, room temperature, 30 min2: 71 percent / benzene / 5 h / 70 °C3: 88 percent / lithium aluminium hydride / diethyl ether / 2 h / 0 °C4: 96 percent / m-chloroperoxybenzoic acid / CHCl3 / 2 h / -20 °C  

Multi-step reaction with 3 steps 1: 71 percent / benzene / 5 h / 70 °C2: 88 percent / lithium aluminium hydride / diethyl ether / 2 h / 0 °C3: 96 percent / m-chloroperoxybenzoic acid / CHCl3 / 2 h / -20 °C  

Multi-step reaction with 2 steps 1: 88 percent / lithium aluminium hydride / diethyl ether / 2 h / 0 °C2: 96 percent / m-chloroperoxybenzoic acid / CHCl3 / 2 h / -20 °C  

Multi-step reaction with 2 steps 1: 69 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / 0 °C2: 1.) dimethyl sulphide, N-chlorosuccinimide, 2.) triethylamine / 1.) toluene, ether, -20 deg C, 2 h, 2.) 30 min  

Multi-step reaction with 19 steps 1: 69 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / 0 °C2: 1.) dimethyl sulphide, N-chlorosuccinimide, 2.) triethylamine / 1.) toluene, ether, -20 deg C, 2 h, 2.) 30 min3: 63 percent / benzene / 6 h / 80 °C4: 86 percent / ethyl di-isopropylamine / CH2Cl2 / 2 h / Heating5: 70 percent / Dowex 50W X-8 / methanol / 3 h / Ambient temperature6: 95 percent / hydrogen / 10percent Pd-C / methanol / 4 h / 760 Torr7: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min8: 74 percent / butyl-lithium / hexane; tetrahydrofuran / 2 h / 0 °C9: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 1M aq. NaOH, 30percent aq. hydrogen peroxide / 1.) THF, 4 h, reflux, 2.) 0 deg C, 30 min10: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min, room temperature, 15 min11: 1.) butyl-lithium, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) room temperature, 3 h12: 98 percent / sodium hydroxide / methanol; H2O / 3 h / Ambient temperature13: 95 percent / tetrahydrofuran / 12 h14: 87 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 7 h / -78 °C15: 95 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 2 h / -78 °C16: m-chloroperoxybenzoic acid, 30percent aq. hydrogen peroxide / CDCl3 / 1.) -50 deg C, 15 min, 2.) 0 deg C, 15 min17: 37 percent / toluene / 5 h / 100 °C18: 98 percent / sodium hydroxide / H2O; methanol / 2 h / 0 °C19: 65 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1.) -20 deg C, 1 h, 2.) 0 deg C, 12 h  

Multi-step reaction with 21 steps 1: 69 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / 0 °C2: 1.) dimethyl sulphide, N-chlorosuccinimide, 2.) triethylamine / 1.) toluene, ether, -20 deg C, 2 h, 2.) 30 min3: 63 percent / benzene / 6 h / 80 °C4: 86 percent / ethyl di-isopropylamine / CH2Cl2 / 2 h / Heating5: 70 percent / Dowex 50W X-8 / methanol / 3 h / Ambient temperature6: 95 percent / hydrogen / 10percent Pd-C / methanol / 4 h / 760 Torr7: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min8: 74 percent / butyl-lithium / hexane; tetrahydrofuran / 2 h / 0 °C9: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 1M aq. NaOH, 30percent aq. hydrogen peroxide / 1.) THF, 4 h, reflux, 2.) 0 deg C, 30 min10: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min, room temperature, 15 min11: 1.) butyl-lithium, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) room temperature, 3 h12: 98 percent / sodium hydroxide / methanol; H2O / 3 h / Ambient temperature13: 95 percent / tetrahydrofuran / 12 h14: 87 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 7 h / -78 °C15: 95 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 2 h / -78 °C16: m-chloroperoxybenzoic acid, 30percent aq. hydrogen peroxide / CDCl3 / 1.) -50 deg C, 15 min, 2.) 0 deg C, 15 min17: 37 percent / toluene / 5 h / 100 °C18: 98 percent / sodium hydroxide / H2O; methanol / 2 h / 0 °C19: 65 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1.) -20 deg C, 1 h, 2.) 0 deg C, 12 h20: 51 percent / aluminium isopropoxide / o-xylene / 8 h / 125 °C  

Multi-step reaction with 26 steps 1: 69 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / 0 °C2: 1.) dimethyl sulphide, N-chlorosuccinimide, 2.) triethylamine / 1.) toluene, ether, -20 deg C, 2 h, 2.) 30 min3: 63 percent / benzene / 6 h / 80 °C4: 86 percent / ethyl di-isopropylamine / CH2Cl2 / 2 h / Heating5: 70 percent / Dowex 50W X-8 / methanol / 3 h / Ambient temperature6: 95 percent / hydrogen / 10percent Pd-C / methanol / 4 h / 760 Torr7: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min8: 74 percent / butyl-lithium / hexane; tetrahydrofuran / 2 h / 0 °C9: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 1M aq. NaOH, 30percent aq. hydrogen peroxide / 1.) THF, 4 h, reflux, 2.) 0 deg C, 30 min10: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min, room temperature, 15 min11: 1.) butyl-lithium, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) room temperature, 3 h12: 98 percent / sodium hydroxide / methanol; H2O / 3 h / Ambient temperature13: 95 percent / tetrahydrofuran / 12 h14: 87 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 7 h / -78 °C15: 95 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 2 h / -78 °C16: m-chloroperoxybenzoic acid, 30percent aq. hydrogen peroxide / CDCl3 / 1.) -50 deg C, 15 min, 2.) 0 deg C, 15 min17: 37 percent / toluene / 5 h / 100 °C18: 98 percent / sodium hydroxide / H2O; methanol / 2 h / 0 °C19: 65 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1.) -20 deg C, 1 h, 2.) 0 deg C, 12 h20: 51 percent / aluminium isopropoxide / o-xylene / 8 h / 125 °C22: lithium di-isopropylamide23: tetrabutylammonium fluoride24: hydrogen peroxide, pyridine25: NaBH4 26: pyridine  

With  lithium aluminium tetrahydride in  tetrahydrofuran T=0°C; 2 h;   

Multi-step reaction with 3 steps 1: 69 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / 0 °C2: 1.) dimethyl sulphide, N-chlorosuccinimide, 2.) triethylamine / 1.) toluene, ether, -20 deg C, 2 h, 2.) 30 min3: 63 percent / benzene / 6 h / 80 °C