1: 88 percent / lithium aluminium hydride / diethyl ether / 2 h / 0 °C 2: 96 percent / m-chloroperoxybenzoic acid / CHCl3 / 2 h / -20 °C 3: 69 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / 0 °C 4: 1.) dimethyl sulphide, N-chlorosuccinimide, 2.) triethylamine / 1.) toluene, ether, -20 deg C, 2 h, 2.) 30 min 5: 63 percent / benzene / 6 h / 80 °C 6: 86 percent / ethyl di-isopropylamine / CH2Cl2 / 2 h / Heating 7: 70 percent / Dowex 50W X-8 / methanol / 3 h / Ambient temperature 8: 95 percent / hydrogen / 10percent Pd-C / methanol / 4 h / 760 Torr 9: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min 10: 74 percent / butyl-lithium / hexane; tetrahydrofuran / 2 h / 0 °C 11: 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 12: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min, room temperature, 15 min 13: 1.) butyl-lithium, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) room temperature, 3 h 14: 98 percent / sodium hydroxide / methanol; H2O / 3 h / Ambient temperature 15: 95 percent / tetrahydrofuran / 12 h 16: 87 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 7 h / -78 °C 17: 95 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 2 h / -78 °C 18: m-chloroperoxybenzoic acid, 30percent aq. hydrogen peroxide / CDCl3 / 1.) -50 deg C, 15 min, 2.) 0 deg C, 15 min 19: 37 percent / toluene / 5 h / 100 °C 20: 98 percent / sodium hydroxide / H2O; methanol / 2 h / 0 °C 21: 98 percent / lithium di-isopropylamide / tetrahydrofuran; hexane / 2 h 22: 78 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C 23: 68 percent / pyridine, 30percent aq. hydrogen peroxide / CH2Cl2 / 12 h / Ambient temperature 24: 72 percent / sodium borohydride / ethanol / 3 h / 0 °C 25: 94 percent / pyridine, 4-dimethylaminopyridine / CH2Cl2 / 2 h / Ambient temperature 26: 19 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1.) -20 deg C, 1 h, 2.) 0 deg C, 12 h 27: 67 percent / aluminium isopropoxide / o-xylene / 5 h / 125 °C 28: 40 percent / 5percent aq. HF / acetonitrile / 3 h / Ambient temperature View Scheme

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 4 steps 1: 90 percent / LiAlH4 2: 95 percent / MCPBA3: 60 percent / LiAlH4 4: 95 percent / N-chlorosuccinimide, Me2S, Et3N / CH2Cl2 / -20 °C  

Multi-step reaction with 11 steps 1: 90 percent / LiAlH4 2: 95 percent / MCPBA3: 60 percent / LiAlH4 4: 95 percent / N-chlorosuccinimide, Me2S, Et3N / CH2Cl2 / -20 °C5: 70 percent6: 85 percent / Et2N-i-Pr7: 70 percent / Dowex 50W-X8 8: 95 percent / H2 / Pd/C / methanol9: 90 percent / DMSO, oxalyl chloride10: 70 percent11: 1.) 9-BBN, 2.) H2O2, base  

Multi-step reaction with 13 steps 1: 90 percent / LiAlH4 2: 95 percent / MCPBA3: 60 percent / LiAlH4 4: 95 percent / N-chlorosuccinimide, Me2S, Et3N / CH2Cl2 / -20 °C5: 70 percent6: 85 percent / Et2N-i-Pr7: 70 percent / Dowex 50W-X8 8: 95 percent / H2 / Pd/C / methanol9: 90 percent / DMSO, oxalyl chloride10: 70 percent11: 1.) 9-BBN, 2.) H2O2, base12: 90 percent / DMSO, oxalyl chloride  

Multi-step reaction with 15 steps 1: 90 percent / LiAlH4 2: 95 percent / MCPBA3: 60 percent / LiAlH4 4: 95 percent / N-chlorosuccinimide, Me2S, Et3N / CH2Cl2 / -20 °C5: 70 percent6: 85 percent / Et2N-i-Pr7: 70 percent / Dowex 50W-X8 8: 95 percent / H2 / Pd/C / methanol9: 90 percent / DMSO, oxalyl chloride10: 70 percent11: 1.) 9-BBN, 2.) H2O2, base12: 90 percent / DMSO, oxalyl chloride14: 90 percent / NaOH / methanol; H2O15: 90 percent  

Multi-step reaction with 17 steps 1: 90 percent / LiAlH4 2: 95 percent / MCPBA3: 60 percent / LiAlH4 4: 95 percent / N-chlorosuccinimide, Me2S, Et3N / CH2Cl2 / -20 °C5: 70 percent6: 85 percent / Et2N-i-Pr7: 70 percent / Dowex 50W-X8 8: 95 percent / H2 / Pd/C / methanol9: 90 percent / DMSO, oxalyl chloride10: 70 percent11: 1.) 9-BBN, 2.) H2O2, base12: 90 percent / DMSO, oxalyl chloride14: 90 percent / NaOH / methanol; H2O15: 90 percent16: LiN(SiMe3)217: 95 percent / LiN(SiMe3)2  

Multi-step reaction with 18 steps 1: 90 percent / LiAlH4 2: 95 percent / MCPBA3: 60 percent / LiAlH4 4: 95 percent / N-chlorosuccinimide, Me2S, Et3N / CH2Cl2 / -20 °C5: 70 percent6: 85 percent / Et2N-i-Pr7: 70 percent / Dowex 50W-X8 8: 95 percent / H2 / Pd/C / methanol9: 90 percent / DMSO, oxalyl chloride10: 70 percent11: 1.) 9-BBN, 2.) H2O2, base12: 90 percent / DMSO, oxalyl chloride14: 90 percent / NaOH / methanol; H2O15: 90 percent16: LiN(SiMe3)217: 95 percent / LiN(SiMe3)218: MCPBA, H2O2 / 1.) -40 deg C, 15 min, 2.) 0 deg C  

Multi-step reaction with 23 steps 1: 88 percent / lithium aluminium hydride / diethyl ether / 2 h / 0 °C2: 96 percent / m-chloroperoxybenzoic acid / CHCl3 / 2 h / -20 °C3: 69 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / 0 °C4: 1.) dimethyl sulphide, N-chlorosuccinimide, 2.) triethylamine / 1.) toluene, ether, -20 deg C, 2 h, 2.) 30 min5: 63 percent / benzene / 6 h / 80 °C6: 86 percent / ethyl di-isopropylamine / CH2Cl2 / 2 h / Heating7: 70 percent / Dowex 50W X-8 / methanol / 3 h / Ambient temperature8: 95 percent / hydrogen / 10percent Pd-C / methanol / 4 h / 760 Torr9: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min10: 74 percent / butyl-lithium / hexane; tetrahydrofuran / 2 h / 0 °C11: 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 min12: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min, room temperature, 15 min13: 1.) butyl-lithium, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) room temperature, 3 h14: 98 percent / sodium hydroxide / methanol; H2O / 3 h / Ambient temperature15: 95 percent / tetrahydrofuran / 12 h16: 87 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 7 h / -78 °C17: 95 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 2 h / -78 °C18: m-chloroperoxybenzoic acid, 30percent aq. hydrogen peroxide / CDCl3 / 1.) -50 deg C, 15 min, 2.) 0 deg C, 15 min19: 37 percent / toluene / 5 h / 100 °C20: 98 percent / sodium hydroxide / H2O; methanol / 2 h / 0 °C21: 65 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1.) -20 deg C, 1 h, 2.) 0 deg C, 12 h22: 51 percent / aluminium isopropoxide / o-xylene / 8 h / 125 °C  

Multi-step reaction with 20 steps 1: 90 percent / LiAlH4 2: 95 percent / MCPBA3: 60 percent / LiAlH4 4: 95 percent / N-chlorosuccinimide, Me2S, Et3N / CH2Cl2 / -20 °C5: 70 percent6: 85 percent / Et2N-i-Pr7: 70 percent / Dowex 50W-X8 8: 95 percent / H2 / Pd/C / methanol9: 90 percent / DMSO, oxalyl chloride10: 70 percent11: 1.) 9-BBN, 2.) H2O2, base12: 90 percent / DMSO, oxalyl chloride14: 90 percent / NaOH / methanol; H2O15: 90 percent16: LiN(SiMe3)217: 95 percent / LiN(SiMe3)218: MCPBA, H2O2 / 1.) -40 deg C, 15 min, 2.) 0 deg C19: toluene / 5 h / 80 - 100 °C20: 85 percent / KOH / methanol