1: 90 percent / SOCl2 / pyridine / 0.5 h / Ambient temperature 2: 45 percent / H2 / 5percent rhodium om alumina / ethyl acetate / 2 h / 2432 Torr 3: 94 percent / 5percent KOH-MeOH / 1 h / Heating View Scheme

1: 71 percent / DBU / benzene / 0.5 h / Heating 2: 92 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr 3: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature 4: 83 mg / triethylamine / CH2Cl2 / 0.17 h / 0 °C 5: 65 mg / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature 6: 82 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature 7: 1.) CH3COOH, H2O, pyridine, 2.) 4-(N,N-dimethylamino)pyridine / 1.) reflux, 4 h, 2.) RT, 10 h 8: 94 percent / 5percent KOH-MeOH / 1 h / Heating View Scheme

1: 92 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr 2: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature 3: 83 mg / triethylamine / CH2Cl2 / 0.17 h / 0 °C 4: 65 mg / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature 5: 82 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature 6: 1.) CH3COOH, H2O, pyridine, 2.) 4-(N,N-dimethylamino)pyridine / 1.) reflux, 4 h, 2.) RT, 10 h 7: 94 percent / 5percent KOH-MeOH / 1 h / Heating View Scheme

1: 1.) n-BuLi / 1.) THF, room temperature, 30 min, 2.) -78 deg C, 1.5 h 2: 1.) MeSO2X, 2.) potassium superoxide, 18-crown-6 / 2.) DMF, DMSO 3: 3.4 g / H2 / Lindlar catalyst / diethyl ether; ethanol / 3 h 4: 85 percent / 70percent t-butyl hydroperoxide, vanadyloxy acetylacetonate / benzene / 2.5 h / Ambient temperature 5: 1.)Et3Al, 2.) 2M HCl / 1.) THF, hexane, 0 deg C, 16 h, 2.) MeOH, THF, room temperature, 1 h 6: 56 percent / toluene-p-sulphonic acid / 17 h / Ambient temperature 7: 65 percent / di-isobitylaluminium hydride / tetrahydrofuran; hexane / 5 h / Ambient temperature 8: 580 mg / pyridine / 16 h / Ambient temperature 9: NaBH4 / methanol; tetrahydrofuran / 3 h / Ambient temperature 10: 260 mg / pyridine / 3 h / Ambient temperature 11: 96 percent / NaI / acetone / 72 h / Heating 12: 98 percent / Bu3SnH / tetrahydrofuran / 18 h / Ambient temperature 13: 396 mg / 5percent KOH-MeOH / tetrahydrofuran / 1 h / Ambient temperature 14: pyridine / 2 h / Ambient temperature 15: 1.) BF3-THF complex, 2.) 2N NaOH, 30percent H2O2, 3.) pyridinium chloroformate 16: 209 mg / LiBr / dimethylformamide / 1 h / Heating 17: 220 mg / OsO4, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h 18: 70percent AcOH / H2O / 4 h / 65 °C View Scheme

1: 1.) n-BuLi / 1.) THF, room temperature, 30 min, 2.) -78 deg C, 1.5 h 2: 1.) MeSO2X, 2.) potassium superoxide, 18-crown-6 / 2.) DMF, DMSO 3: 3.4 g / H2 / Lindlar catalyst / diethyl ether; ethanol / 3 h 4: 85 percent / 70percent t-butyl hydroperoxide, vanadyloxy acetylacetonate / benzene / 2.5 h / Ambient temperature 5: 1.)Et3Al, 2.) 2M HCl / 1.) THF, hexane, 0 deg C, 16 h, 2.) MeOH, THF, room temperature, 1 h 6: 56 percent / toluene-p-sulphonic acid / 17 h / Ambient temperature 7: 65 percent / di-isobitylaluminium hydride / tetrahydrofuran; hexane / 5 h / Ambient temperature 8: 580 mg / pyridine / 16 h / Ambient temperature 9: NaBH4 / methanol; tetrahydrofuran / 3 h / Ambient temperature 10: 260 mg / pyridine / 3 h / Ambient temperature 11: 96 percent / NaI / acetone / 72 h / Heating 12: 98 percent / Bu3SnH / tetrahydrofuran / 18 h / Ambient temperature 13: 396 mg / 5percent KOH-MeOH / tetrahydrofuran / 1 h / Ambient temperature 14: pyridine / 2 h / Ambient temperature 15: 1.) BF3-THF complex, 2.) 2N NaOH, 30percent H2O2, 3.) pyridinium chloroformate 16: 209 mg / LiBr / dimethylformamide / 1 h / Heating 17: 220 mg / OsO4, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h 18: 70percent AcOH / H2O / 4 h / 65 °C View Scheme

1: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C 2: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature 3: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h 4: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 5: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 6: 96 percent / CSA / 24 h / Ambient temperature 7: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 8: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating 9: 98 percent / aq. TFA / methanol / 1 h View Scheme

1: 1.) MeSO2X, 2.) potassium superoxide, 18-crown-6 / 2.) DMF, DMSO 2: 3.4 g / H2 / Lindlar catalyst / diethyl ether; ethanol / 3 h 3: 85 percent / 70percent t-butyl hydroperoxide, vanadyloxy acetylacetonate / benzene / 2.5 h / Ambient temperature 4: 1.)Et3Al, 2.) 2M HCl / 1.) THF, hexane, 0 deg C, 16 h, 2.) MeOH, THF, room temperature, 1 h 5: 56 percent / toluene-p-sulphonic acid / 17 h / Ambient temperature 6: 65 percent / di-isobitylaluminium hydride / tetrahydrofuran; hexane / 5 h / Ambient temperature 7: 580 mg / pyridine / 16 h / Ambient temperature 8: NaBH4 / methanol; tetrahydrofuran / 3 h / Ambient temperature 9: 260 mg / pyridine / 3 h / Ambient temperature 10: 96 percent / NaI / acetone / 72 h / Heating 11: 98 percent / Bu3SnH / tetrahydrofuran / 18 h / Ambient temperature 12: 396 mg / 5percent KOH-MeOH / tetrahydrofuran / 1 h / Ambient temperature 13: pyridine / 2 h / Ambient temperature 14: 1.) BF3-THF complex, 2.) 2N NaOH, 30percent H2O2, 3.) pyridinium chloroformate 15: 209 mg / LiBr / dimethylformamide / 1 h / Heating 16: 220 mg / OsO4, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h 17: 70percent AcOH / H2O / 4 h / 65 °C View Scheme

1: 3.4 g / H2 / Lindlar catalyst / diethyl ether; ethanol / 3 h 2: 85 percent / 70percent t-butyl hydroperoxide, vanadyloxy acetylacetonate / benzene / 2.5 h / Ambient temperature 3: 1.)Et3Al, 2.) 2M HCl / 1.) THF, hexane, 0 deg C, 16 h, 2.) MeOH, THF, room temperature, 1 h 4: 56 percent / toluene-p-sulphonic acid / 17 h / Ambient temperature 5: 65 percent / di-isobitylaluminium hydride / tetrahydrofuran; hexane / 5 h / Ambient temperature 6: 580 mg / pyridine / 16 h / Ambient temperature 7: NaBH4 / methanol; tetrahydrofuran / 3 h / Ambient temperature 8: 260 mg / pyridine / 3 h / Ambient temperature 9: 96 percent / NaI / acetone / 72 h / Heating 10: 98 percent / Bu3SnH / tetrahydrofuran / 18 h / Ambient temperature 11: 396 mg / 5percent KOH-MeOH / tetrahydrofuran / 1 h / Ambient temperature 12: pyridine / 2 h / Ambient temperature 13: 1.) BF3-THF complex, 2.) 2N NaOH, 30percent H2O2, 3.) pyridinium chloroformate 14: 209 mg / LiBr / dimethylformamide / 1 h / Heating 15: 220 mg / OsO4, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h 16: 70percent AcOH / H2O / 4 h / 65 °C View Scheme

1: 70 percent / tetrahydrofuran / Ambient temperature 2: 1) 4N NaOH, 30percent H2O2, 2) Ac2O, pyridine / 1) EtOH, 35 deg C, 4h, 2) RT, overnight 3: 72 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature 4: 100 percent / 30percent HClO4 / methanol / 0.17 h / 0 °C 5: 95.5 percent / PDC / CH2Cl2 / 5 h / Ambient temperature 6: 88 percent / H2 / PtO2 / ethyl acetate; ethanol / 3 h / Ambient temperature 7: 96 percent / LiAlH4 / tetrahydrofuran / 4 h / Ambient temperature 8: p-TsOH / 0.33 h / Ambient temperature 9: CrO3, pyridine / 5 h / Ambient temperature 10: 2) 5percent HCl / 2) (PH3P)3RhCl / 1) toluene, 2h, reflux, 2) MeOH, overnight 11: 52 percent / Zn(Hg), TMSCl / tetrahydrofuran / 12 h / Ambient temperature 12: 93 percent / OsO4, NMMNO / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 22 h / Ambient temperature View Scheme

1: 96 percent / LiAlH4 / tetrahydrofuran / 4 h / Ambient temperature 2: p-TsOH / 0.33 h / Ambient temperature 3: CrO3, pyridine / 5 h / Ambient temperature 4: 2) 5percent HCl / 2) (PH3P)3RhCl / 1) toluene, 2h, reflux, 2) MeOH, overnight 5: 52 percent / Zn(Hg), TMSCl / tetrahydrofuran / 12 h / Ambient temperature 6: 93 percent / OsO4, NMMNO / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 22 h / Ambient temperature View Scheme