1: 80 percent / NaN3, 18-crown-6 / dimethylformamide / 1.5 h / 100 °C 2: 94 percent / CrO3, H2SO4 / H2O; acetone / 1.5 h / Ambient temperature 3: 1.) PPh3, 2.) NaBH3CN / 1.) THF, rt, 12 h, 2.) MeOH, AcOH, 12 h 4: 42 percent / H2O; formic acid / 12 h / 120 °C View Scheme

1: 1.) PPh3, 2.) NaBH3CN / 1.) THF, rt, 12 h, 2.) MeOH, AcOH, 12 h 2: 42 percent / H2O; formic acid / 12 h / 120 °C View Scheme

1: 57 mg / DBU / CH2Cl2 / 1 h / Ambient temperature 2: 1.) BH3*Me2S, 2.) H2O2, NaOH / 1.) THF, rt, 4.5 h, 2.) THF, H2O, rt, 12 h 3: CH2Cl2; triethylamine / 1.5 h / Ambient temperature 4: 80 percent / NaN3, 18-crown-6 / dimethylformamide / 1.5 h / 100 °C 5: 94 percent / CrO3, H2SO4 / H2O; acetone / 1.5 h / Ambient temperature 6: 1.) PPh3, 2.) NaBH3CN / 1.) THF, rt, 12 h, 2.) MeOH, AcOH, 12 h 7: 42 percent / H2O; formic acid / 12 h / 120 °C View Scheme

1: CuI / tetrahydrofuran / -78 °C 2: Et3N / tetrahydrofuran / -78 - 20 °C 3: 3.54 g / NaI, m-CPBA / tetrahydrofuran / 0.33 h / Ambient temperature 4: Bu3SnH, AIBN / benzene / 1 h / Heating 5: 84 percent / TFA / benzene / 0.33 h 6: BF3*Et2O / CH2Cl2 / 3.5 h 7: 57 mg / DBU / CH2Cl2 / 1 h / Ambient temperature 8: 1.) BH3*Me2S, 2.) H2O2, NaOH / 1.) THF, rt, 4.5 h, 2.) THF, H2O, rt, 12 h 9: CH2Cl2; triethylamine / 1.5 h / Ambient temperature 10: 80 percent / NaN3, 18-crown-6 / dimethylformamide / 1.5 h / 100 °C 11: 94 percent / CrO3, H2SO4 / H2O; acetone / 1.5 h / Ambient temperature 12: 1.) PPh3, 2.) NaBH3CN / 1.) THF, rt, 12 h, 2.) MeOH, AcOH, 12 h 13: 42 percent / H2O; formic acid / 12 h / 120 °C View Scheme

1: 55 percent / PTSA*H2O / CH2Cl2 / 1 h / Heating 2: CuI / tetrahydrofuran / -78 °C 3: Et3N / tetrahydrofuran / -78 - 20 °C 4: 3.54 g / NaI, m-CPBA / tetrahydrofuran / 0.33 h / Ambient temperature 5: Bu3SnH, AIBN / benzene / 1 h / Heating 6: 84 percent / TFA / benzene / 0.33 h 7: BF3*Et2O / CH2Cl2 / 3.5 h 8: 57 mg / DBU / CH2Cl2 / 1 h / Ambient temperature 9: 1.) BH3*Me2S, 2.) H2O2, NaOH / 1.) THF, rt, 4.5 h, 2.) THF, H2O, rt, 12 h 10: CH2Cl2; triethylamine / 1.5 h / Ambient temperature 11: 80 percent / NaN3, 18-crown-6 / dimethylformamide / 1.5 h / 100 °C 12: 94 percent / CrO3, H2SO4 / H2O; acetone / 1.5 h / Ambient temperature 13: 1.) PPh3, 2.) NaBH3CN / 1.) THF, rt, 12 h, 2.) MeOH, AcOH, 12 h 14: 42 percent / H2O; formic acid / 12 h / 120 °C View Scheme

1: 84 percent / TFA / benzene / 0.33 h 2: BF3*Et2O / CH2Cl2 / 3.5 h 3: 57 mg / DBU / CH2Cl2 / 1 h / Ambient temperature 4: 1.) BH3*Me2S, 2.) H2O2, NaOH / 1.) THF, rt, 4.5 h, 2.) THF, H2O, rt, 12 h 5: CH2Cl2; triethylamine / 1.5 h / Ambient temperature 6: 80 percent / NaN3, 18-crown-6 / dimethylformamide / 1.5 h / 100 °C 7: 94 percent / CrO3, H2SO4 / H2O; acetone / 1.5 h / Ambient temperature 8: 1.) PPh3, 2.) NaBH3CN / 1.) THF, rt, 12 h, 2.) MeOH, AcOH, 12 h 9: 42 percent / H2O; formic acid / 12 h / 120 °C View Scheme

1.1: tetrahydrofuran / 2 h / 20 °C 2.1: Et3N / tetrahydrofuran / 12 h / 20 °C 3.1: 24.5 g / Et3N / tetrahydrofuran / 2 h / 20 °C 4.1: 71 percent / Bu3SnH; 1,1'-azobis(cyclohexanecarbonitrile) / toluene / 3 h / Heating 5.1: 570 mg / KOH; H2O / ethanol / 2 h / Heating 6.1: K2CO3 / acetonitrile; toluene / 18 h / 20 °C 7.1: 1.34 g / pyridine; DMAP / CH2Cl2 / 3 h / 20 °C 8.1: CH2Cl2 / 1 h / 20 °C 8.2: 4-methylmorpholine N-oxide monohydrate / acetonitrile / 4 h / 20 °C 9.1: 542 mg / H2 / Pd/C / methanol / 1 h / 760 Torr 10.1: HMDS / CH2Cl2 / 1.25 h / -20 - 20 °C 11.1: 779 mg / tetrahydrofuran / 4 h / -78 - 20 °C 12.1: 60 percent / mCPBA / tetrahydrofuran / 1.5 h / -40 - 20 °C 13.1: 77 percent / toluene / 1 h / 70 °C 14.1: NaBH4 / ethanol / 5 h / 20 °C 15.1: 77 percent / DMAP / CH2Cl2 / 2 h / 20 °C 16.1: 83 percent / Bu3SnH; 1,1'-azobis(cyclohexanecarbonitrile) / toluene / 2 h / Heating 17.1: NaOMe / methanol / 24 h / 100 °C 18.1: 8 mg / PTSA / dioxane; H2O / 24 h / 120 °C View Scheme

1.1: water; acetic acid / 2 h / 20 - 50 °C 2.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere 3.1: pyridine; hydrogen fluoride / tetrahydrofuran / 7 h / 0 - 20 °C / Inert atmosphere 4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere 4.2: -78 - 20 °C / Inert atmosphere 5.1: tert.-butyl lithium / diethyl ether; pentane / 0.08 h / -78 °C / Inert atmosphere 5.2: 0.67 h / 0 °C / Inert atmosphere 5.3: 3.5 h / 0 - 20 °C / Inert atmosphere 6.1: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 20 °C / Inert atmosphere 7.1: n-butyllithium; chloro-trimethyl-silane; triethylamine; diisopropylamine / tetrahydrofuran; hexanes / -78 - 20 °C / Inert atmosphere 7.2: 120 °C / Inert atmosphere 8.1: methanol; diethyl ether; benzene / 1.5 h / 6 - 20 °C / Inert atmosphere 9.1: pyridine; hydrogen fluoride / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere 10.1: pyridinium chlorochromate / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere; Celite 11.1: toluene / 110 °C / Inert atmosphere; Molecular sieve; Sealed tube 11.2: 5.58 h / 0 - 20 °C / Molecular sieve 12.1: PHT / tetrahydrofuran / 72 h / 20 °C / Inert atmosphere 12.2: 12 h / 20 °C / Inert atmosphere 13.1: sodium tetrahydroborate / isopropyl alcohol / 77 h / 20 - 50 °C / Inert atmosphere View Scheme

1.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere 2.1: pyridine; hydrogen fluoride / tetrahydrofuran / 7 h / 0 - 20 °C / Inert atmosphere 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere 3.2: -78 - 20 °C / Inert atmosphere 4.1: tert.-butyl lithium / diethyl ether; pentane / 0.08 h / -78 °C / Inert atmosphere 4.2: 0.67 h / 0 °C / Inert atmosphere 4.3: 3.5 h / 0 - 20 °C / Inert atmosphere 5.1: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 20 °C / Inert atmosphere 6.1: n-butyllithium; chloro-trimethyl-silane; triethylamine; diisopropylamine / tetrahydrofuran; hexanes / -78 - 20 °C / Inert atmosphere 6.2: 120 °C / Inert atmosphere 7.1: methanol; diethyl ether; benzene / 1.5 h / 6 - 20 °C / Inert atmosphere 8.1: pyridine; hydrogen fluoride / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere 9.1: pyridinium chlorochromate / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere; Celite 10.1: toluene / 110 °C / Inert atmosphere; Molecular sieve; Sealed tube 10.2: 5.58 h / 0 - 20 °C / Molecular sieve 11.1: PHT / tetrahydrofuran / 72 h / 20 °C / Inert atmosphere 11.2: 12 h / 20 °C / Inert atmosphere 12.1: sodium tetrahydroborate / isopropyl alcohol / 77 h / 20 - 50 °C / Inert atmosphere View Scheme

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: tert.-butyl lithium / diethyl ether; pentane / 0.08 h / -78 °C / Inert atmosphere 2.2: 0.67 h / 0 °C / Inert atmosphere 2.3: 3.5 h / 0 - 20 °C / Inert atmosphere 3.1: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 20 °C / Inert atmosphere 4.1: n-butyllithium; chloro-trimethyl-silane; triethylamine; diisopropylamine / tetrahydrofuran; hexanes / -78 - 20 °C / Inert atmosphere 4.2: 120 °C / Inert atmosphere 5.1: methanol; diethyl ether; benzene / 1.5 h / 6 - 20 °C / Inert atmosphere 6.1: pyridine; hydrogen fluoride / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere 7.1: pyridinium chlorochromate / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere; Celite 8.1: toluene / 110 °C / Inert atmosphere; Molecular sieve; Sealed tube 8.2: 5.58 h / 0 - 20 °C / Molecular sieve 9.1: PHT / tetrahydrofuran / 72 h / 20 °C / Inert atmosphere 9.2: 12 h / 20 °C / Inert atmosphere 10.1: sodium tetrahydroborate / isopropyl alcohol / 77 h / 20 - 50 °C / Inert atmosphere View Scheme