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

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

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