1: 93 percent / oxalyl chloride; TEA; DMSO / CH2Cl2 / -78 °C 2: 60 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C 3: 92 percent / TFA / CH2Cl2 / 1 h / 0 °C View Scheme

1: 60 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C 2: 92 percent / TFA / CH2Cl2 / 1 h / 0 °C View Scheme

1.1: DIBALH / CH2Cl2 / -30 °C 2.1: SO3*Py; TEA / CH2Cl2 / 0 °C 3.1: LDA; ZnCl2 / tetrahydrofuran / -78 - -40 °C 3.2: tetrahydrofuran / 1 h / -50 °C 4.1: 2,6-lutidine / CH2Cl2 / 0 - 20 °C 5.1: H2O; acetic acid / 20 °C 6.1: 2,4,6-trichlorobenzoyl chloride; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C 6.2: 70 percent / H2SiF6 / 2-methyl-propan-2-ol; acetonitrile; CH2Cl2 / 24 h / 20 °C 7.1: 93 percent / oxalyl chloride; TEA; DMSO / CH2Cl2 / -78 °C 8.1: 60 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C 9.1: 92 percent / TFA / CH2Cl2 / 1 h / 0 °C View Scheme

1: 92 percent / 2 h / 100 °C 2: 1.) NaHMDS / 1.) THF, 0 deg C, 0.25 h, 2.) 0 deg C, 15 min 3: 86 percent / CSA / CH2Cl2; methanol / 1.) 0 deg C, 1 h, 2.) 25 deg C, 0.5 h 4: 82 percent / SO3*pyridine, DMSO, Et3N / CH2Cl2 / 0.5 h / 25 °C 5: LDA / tetrahydrofuran / 1.) -78 to -40 deg C, 0.5 h, 2.) -78 deg C 6: 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 7: K2CO3 / methanol / 0.25 h / 25 °C 8: 79 percent / TBAF / tetrahydrofuran / 8 h / 25 °C 9: 1.) 2,4,6-trichlorobenzoylchloride, Et3N, 2.) 4-DMAP / 1.) THF, 25 deg C, 15 min, 2.) toluene, 25 deg C, 0.5 h 10: 92 percent / CF3COOH / CH2Cl2 / 1 h / 0 °C View Scheme

1: 86 percent / CSA / CH2Cl2; methanol / 1.) 0 deg C, 1 h, 2.) 25 deg C, 0.5 h 2: 82 percent / SO3*pyridine, DMSO, Et3N / CH2Cl2 / 0.5 h / 25 °C 3: LDA / tetrahydrofuran / 1.) -78 to -40 deg C, 0.5 h, 2.) -78 deg C 4: 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 5: K2CO3 / methanol / 0.25 h / 25 °C 6: 79 percent / TBAF / tetrahydrofuran / 8 h / 25 °C 7: 1.) 2,4,6-trichlorobenzoylchloride, Et3N, 2.) 4-DMAP / 1.) THF, 25 deg C, 15 min, 2.) toluene, 25 deg C, 0.5 h 8: 92 percent / CF3COOH / CH2Cl2 / 1 h / 0 °C View Scheme

1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C / |Inert atmosphere 1.2: 0.25 h / -78 °C / |Inert atmosphere 2.1: 2,6-dimethylpyridine / tetrahydrofuran / 0.5 h / -50 °C / |Inert atmosphere 3.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1 h / -78 - -40 °C / |Inert atmosphere 3.2: 0 - 22 °C / |Inert atmosphere 4.1: sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 3 h / 22 °C / |Inert atmosphere 5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / 22 °C / |Inert atmosphere 6.1: C52H67Cl2NOW / benzene; toluene / 2.5 h / 22 °C / 1 Torr / |Inert atmosphere; |Glovebox 7.1: pyridine hydrogenfluoride / tetrahydrofuran / 36 h / 22 °C / |Inert atmosphere View Scheme

1: C52H67Cl2NOW / benzene; toluene / 2.5 h / 22 °C / 1 Torr / |Inert atmosphere; |Glovebox 2: pyridine hydrogenfluoride / tetrahydrofuran / 36 h / 22 °C / |Inert atmosphere View Scheme

1.1: 1H-imidazole / dichloromethane / 14 h / 22 °C / |Inert atmosphere 2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C / |Inert atmosphere 2.2: 0.25 h / -78 °C / |Inert atmosphere 3.1: 2,6-dimethylpyridine / tetrahydrofuran / 0.5 h / -50 °C / |Inert atmosphere 4.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1 h / -78 - -40 °C / |Inert atmosphere 4.2: 0 - 22 °C / |Inert atmosphere 5.1: sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 3 h / 22 °C / |Inert atmosphere 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / 22 °C / |Inert atmosphere 7.1: C52H67Cl2NOW / benzene; toluene / 2.5 h / 22 °C / 1 Torr / |Inert atmosphere; |Glovebox 8.1: pyridine hydrogenfluoride / tetrahydrofuran / 36 h / 22 °C / |Inert atmosphere View Scheme

1.1: sodium tetrahydroborate / dichloromethane; ethanol / 2 h / -78 °C / |Inert atmosphere 1.2: 22 °C / |Inert atmosphere 2.1: 1H-imidazole / dichloromethane / 14 h / 22 °C / |Inert atmosphere 3.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C / |Inert atmosphere 3.2: 0.25 h / -78 °C / |Inert atmosphere 4.1: 2,6-dimethylpyridine / tetrahydrofuran / 0.5 h / -50 °C / |Inert atmosphere 5.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1 h / -78 - -40 °C / |Inert atmosphere 5.2: 0 - 22 °C / |Inert atmosphere 6.1: sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 3 h / 22 °C / |Inert atmosphere 7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / 22 °C / |Inert atmosphere 8.1: C52H67Cl2NOW / benzene; toluene / 2.5 h / 22 °C / 1 Torr / |Inert atmosphere; |Glovebox 9.1: pyridine hydrogenfluoride / tetrahydrofuran / 36 h / 22 °C / |Inert atmosphere View Scheme

1.1: ozone; oxygen / dichloromethane / -78 °C / |Inert atmosphere 2.1: dimethylsulfide / 168 h / 22 °C / |Inert atmosphere 3.1: sodium tetrahydroborate / dichloromethane; ethanol / 2 h / -78 °C / |Inert atmosphere 3.2: 22 °C / |Inert atmosphere 4.1: 1H-imidazole / dichloromethane / 14 h / 22 °C / |Inert atmosphere 5.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C / |Inert atmosphere 5.2: 0.25 h / -78 °C / |Inert atmosphere 6.1: 2,6-dimethylpyridine / tetrahydrofuran / 0.5 h / -50 °C / |Inert atmosphere 7.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1 h / -78 - -40 °C / |Inert atmosphere 7.2: 0 - 22 °C / |Inert atmosphere 8.1: sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 3 h / 22 °C / |Inert atmosphere 9.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / 22 °C / |Inert atmosphere 10.1: C52H67Cl2NOW / benzene; toluene / 2.5 h / 22 °C / 1 Torr / |Inert atmosphere; |Glovebox 11.1: pyridine hydrogenfluoride / tetrahydrofuran / 36 h / 22 °C / |Inert atmosphere View Scheme