1: 88 percent / iPr2EtN / CH2Cl2 2: K2CO3 / methanol 3: NBS / CH2Cl2 4: 86 percent / OsO4, N-methylmorpholine N-oxide / tetrahydrofuran; H2O 5: 97 percent / iPr2EtN / CH2Cl2 6: 79 percent / Zn, AcOH / ethanol 7: 86 percent / NaHCO3 / diphenyl ether / 0.5 h / 260 °C 8: Et3N, DMAP / CH2Cl2 / 0 °C 9: Bu3SnH, AIBN / benzene / 80 °C 10: 30percent H2O2, KHCO3 / methanol; tetrahydrofuran / Heating 11: 100 percent / imidazole / dimethylformamide 12: iPrEtN, DMAP / CH2Cl2 13: TBAF / tetrahydrofuran 14: SO3*Py, Et3N / dimethylsulfoxide 15: NaClO2, NaH2PO4*2H2O, 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O 16: CH2Cl2 17: 98 percent / AcCl / methanol View Scheme

1: 88 percent / iPr2EtN / CH2Cl2 2: K2CO3 / methanol 3: NBS / CH2Cl2 4: 86 percent / OsO4, N-methylmorpholine N-oxide / tetrahydrofuran; H2O 5: 97 percent / iPr2EtN / CH2Cl2 6: 79 percent / Zn, AcOH / ethanol 7: 86 percent / NaHCO3 / diphenyl ether / 0.5 h / 260 °C View Scheme

1: 88 percent / iPr2EtN / CH2Cl2 2: K2CO3 / methanol 3: NBS / CH2Cl2 4: 86 percent / OsO4, N-methylmorpholine N-oxide / tetrahydrofuran; H2O 5: 97 percent / iPr2EtN / CH2Cl2 6: 79 percent / Zn, AcOH / ethanol 7: 86 percent / NaHCO3 / diphenyl ether / 0.5 h / 260 °C 8: Et3N, DMAP / CH2Cl2 / 0 °C 9: Bu3SnH, AIBN / benzene / 80 °C 10: 30percent H2O2, KHCO3 / methanol; tetrahydrofuran / Heating 11: 100 percent / imidazole / dimethylformamide 12: iPrEtN, DMAP / CH2Cl2 13: TBAF / tetrahydrofuran 14: SO3*Py, Et3N / dimethylsulfoxide 15: NaClO2, NaH2PO4*2H2O, 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O 16: CH2Cl2 17: 98 percent / AcCl / methanol 18: 96 percent / aq. 1 M NaOH / tetrahydrofuran; H2O View Scheme

1: 95 percent / PDC / CH2Cl2 2: 93 percent / lipase PS (Pseudomonas sp., Amano); phosphate buffer / 21 h / 20 °C / pH 7.6 3: 98 percent / imidazole / dimethylformamide 4: 64 percent / lithium 2-thienylcyanocuprate; BF3*Et2O / tetrahydrofuran; diethyl ether / -78 °C 5: 83 percent / NaBH4 / methanol 6: 73 percent / NaHCO3 / diphenyl ether / 0.5 h / 280 °C 7: 77 percent / H2 / PtO2 / ethyl acetate 8: 90 percent / pyridine; DMAP / CH2Cl2 / 20 °C 9: 84 percent / NaN3 / dimethylformamide / 5 h / 20 °C 10: 90 percent / TBAF / tetrahydrofuran 11: 92 percent / pyridine; DMAP / CH2Cl2 / 20 °C 12: H2 / 10 percent Pd/C / ethanol 13: acetonitrile / 10 h / Heating 14: NaOH / dioxane 15: 49 percent / POCl3 / 0 - 95 °C 16: 60 percent / HCl; H2O / tetrahydrofuran / 60 °C View Scheme