1: m-chloroperoxybenzoic acid, 30percent aq. hydrogen peroxide / CDCl3 / 1.) -50 deg C, 15 min, 2.) 0 deg C, 15 min 2: 37 percent / toluene / 5 h / 100 °C 3: 98 percent / sodium hydroxide / H2O; methanol / 2 h / 0 °C 4: 98 percent / lithium di-isopropylamide / tetrahydrofuran; hexane / 2 h 5: 78 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C 6: 68 percent / pyridine, 30percent aq. hydrogen peroxide / CH2Cl2 / 12 h / Ambient temperature 7: 72 percent / sodium borohydride / ethanol / 3 h / 0 °C 8: 94 percent / pyridine, 4-dimethylaminopyridine / CH2Cl2 / 2 h / Ambient temperature 9: 19 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1.) -20 deg C, 1 h, 2.) 0 deg C, 12 h 10: 67 percent / aluminium isopropoxide / o-xylene / 5 h / 125 °C 11: 40 percent / 5percent aq. HF / acetonitrile / 3 h / Ambient temperature View Scheme

Multi-step reaction with 14 steps 1: 95 percent / N-chlorosuccinimide, Me2S, Et3N / CH2Cl2 / -20 °C2: 70 percent3: 85 percent / Et2N-i-Pr4: 70 percent / Dowex 50W-X8 5: 95 percent / H2 / Pd/C / methanol6: 90 percent / DMSO, oxalyl chloride7: 70 percent8: 1.) 9-BBN, 2.) H2O2, base9: 90 percent / DMSO, oxalyl chloride11: 90 percent / NaOH / methanol; H2O12: 90 percent13: LiN(SiMe3)214: 95 percent / LiN(SiMe3)2  

Multi-step reaction with 13 steps 1: 70 percent2: 85 percent / Et2N-i-Pr3: 70 percent / Dowex 50W-X8 4: 95 percent / H2 / Pd/C / methanol5: 90 percent / DMSO, oxalyl chloride6: 70 percent7: 1.) 9-BBN, 2.) H2O2, base8: 90 percent / DMSO, oxalyl chloride10: 90 percent / NaOH / methanol; H2O11: 90 percent12: LiN(SiMe3)213: 95 percent / LiN(SiMe3)2  

Multi-step reaction with 12 steps 1: 85 percent / Et2N-i-Pr2: 70 percent / Dowex 50W-X8 3: 95 percent / H2 / Pd/C / methanol4: 90 percent / DMSO, oxalyl chloride5: 70 percent6: 1.) 9-BBN, 2.) H2O2, base7: 90 percent / DMSO, oxalyl chloride9: 90 percent / NaOH / methanol; H2O10: 90 percent11: LiN(SiMe3)212: 95 percent / LiN(SiMe3)2  

Multi-step reaction with 10 steps 1: 95 percent / H2 / Pd/C / methanol2: 90 percent / DMSO, oxalyl chloride3: 70 percent4: 1.) 9-BBN, 2.) H2O2, base5: 90 percent / DMSO, oxalyl chloride7: 90 percent / NaOH / methanol; H2O8: 90 percent9: LiN(SiMe3)210: 95 percent / LiN(SiMe3)2  

Multi-step reaction with 11 steps 1: 70 percent / Dowex 50W-X8 2: 95 percent / H2 / Pd/C / methanol3: 90 percent / DMSO, oxalyl chloride4: 70 percent5: 1.) 9-BBN, 2.) H2O2, base6: 90 percent / DMSO, oxalyl chloride8: 90 percent / NaOH / methanol; H2O9: 90 percent10: LiN(SiMe3)211: 95 percent / LiN(SiMe3)2  

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