2: NaHCO3 / methanol / 0 °C 3: DEAD, Ph3P, PPTS / tetrahydrofuran / 0 °C 4: imidazole / dimethylformamide / 20 °C 5: DMAP, Et3N / CH2Cl2 / 20 °C 6: 88 percent / aq. HCl / methanol / 20 °C View Scheme

1: 1.) acetic acid, HBr 2.) KOH / 1.) >15 deg C, 3-5h; 2.) methanol, water, 10 min 2: 63 percent / perchloric acid / CHCl3 / 48 h / 60 °C 3: triethylamine / CHCl3 / 2 h 4: CHCl3 / 5 h / 60 °C 5: HCl, water / palladium-charcoal 10percent / methanol / 48 h / Heating 6: HCl, H2 / palladium-charcoal 10percent / methanol; H2O / 3 h View Scheme

1: 1.) Mg / 1.) THF; 2.) THF, room temperature, 1h 2: 93 percent / NaIO4 / ethanol; H2O / 0.5 h 3: 99 percent / hydroxylamine hydrochloride / pyridine / 3 h 4: pyridine / 1 h / 60 °C 5: HCl / methanol; H2O / 3 h / Heating 6: 1.) acetic acid, HBr 2.) KOH / 1.) >15 deg C, 3-5h; 2.) methanol, water, 10 min 7: 63 percent / perchloric acid / CHCl3 / 48 h / 60 °C 8: triethylamine / CHCl3 / 2 h 9: CHCl3 / 5 h / 60 °C 10: HCl, water / palladium-charcoal 10percent / methanol / 48 h / Heating 11: HCl, H2 / palladium-charcoal 10percent / methanol; H2O / 3 h View Scheme

hydrogenchloride; hydrogen; palladium on activated charcoal in methanol; water 3 h; Yield given;

1: 77 percent / tetrahydrofuran 2: NaIO4 3: NH2OH*HCl, pyridine 4: pyridine 5: LiAlH4 / diethyl ether 6: 1.) HCl, H2O, 2.) HBr / 1.) MeOH, reflux, 2.) 10 deg C 7: KOH, H2O / methanol 8: HClO4 / CHCl3 / 60 °C 9: 1.) Et3N, 2.) pyridine / 1.) CHCl3 10: 1.) dil. HCl, 2.) H2, HCl / 1.) Pd/C, 2.) Pd/C / 1.) MeOH, reflux, 2.) MeOH View Scheme

1: 1.) HCl, H2O, 2.) HBr / 1.) MeOH, reflux, 2.) 10 deg C 2: KOH, H2O / methanol 3: HClO4 / CHCl3 / 60 °C 4: 1.) Et3N, 2.) pyridine / 1.) CHCl3 5: 1.) dil. HCl, 2.) H2, HCl / 1.) Pd/C, 2.) Pd/C / 1.) MeOH, reflux, 2.) MeOH View Scheme

sodium acetate in methanol 10 h; Heating; Yield given;

1: D-(-)-DIPT, TBHP, Ti(O-i-Pr)4 / CH2Cl2 / -20 °C 2: Et3N, DMAP / CH2Cl2 3: 85 percent / copper(I) iodide / tetrahydrofuran / -10 °C 4: 94 percent / pyridine / CH2Cl2 / Ambient temperature 5: NaN3 / dimethylformamide / 7 h / 80 °C 6: 2N aq. HCl / 0.5 h 7: 95 percent / OsO4, K3Fe(CN)6, K2CO3, DHQ-CLB, water / 2-methyl-propan-2-ol 8: 89 percent / imidazole / dimethylformamide / 0 °C 9: pyridine / CH2Cl2 / 2 h / Ambient temperature 10: pyridine / 4 h / Ambient temperature 11: 91 percent / n-Bu4NF / tetrahydrofuran / 1 h / 0 °C 12: 90 percent / lithium bromide / acetic acid; tetrahydrofuran / 24 h / Ambient temperature 13: NaOAc / methanol / 10 h / Heating View Scheme

1: Et3N, DMAP / CH2Cl2 2: 85 percent / copper(I) iodide / tetrahydrofuran / -10 °C 3: 94 percent / pyridine / CH2Cl2 / Ambient temperature 4: NaN3 / dimethylformamide / 7 h / 80 °C 5: 2N aq. HCl / 0.5 h 6: 95 percent / OsO4, K3Fe(CN)6, K2CO3, DHQ-CLB, water / 2-methyl-propan-2-ol 7: 89 percent / imidazole / dimethylformamide / 0 °C 8: pyridine / CH2Cl2 / 2 h / Ambient temperature 9: pyridine / 4 h / Ambient temperature 10: 91 percent / n-Bu4NF / tetrahydrofuran / 1 h / 0 °C 11: 90 percent / lithium bromide / acetic acid; tetrahydrofuran / 24 h / Ambient temperature 12: NaOAc / methanol / 10 h / Heating View Scheme

1: 85 percent / copper(I) iodide / tetrahydrofuran / -10 °C 2: 94 percent / pyridine / CH2Cl2 / Ambient temperature 3: NaN3 / dimethylformamide / 7 h / 80 °C 4: 2N aq. HCl / 0.5 h 5: 95 percent / OsO4, K3Fe(CN)6, K2CO3, DHQ-CLB, water / 2-methyl-propan-2-ol 6: 89 percent / imidazole / dimethylformamide / 0 °C 7: pyridine / CH2Cl2 / 2 h / Ambient temperature 8: pyridine / 4 h / Ambient temperature 9: 91 percent / n-Bu4NF / tetrahydrofuran / 1 h / 0 °C 10: 90 percent / lithium bromide / acetic acid; tetrahydrofuran / 24 h / Ambient temperature 11: NaOAc / methanol / 10 h / Heating View Scheme