1: 90 percent / Pig Liver Esterase, NaOH / dimethylsulfoxide; H2O / 3.5 h / 35 °C / pH=6.9-7.4 2: 90 percent / Et3N, 2-chloro-N-methylpyridinium iodide / CH2Cl2 / 0.33 h / 0 - 20 °C 3: 100 percent / DIBAL / toluene / 2 h / -78 °C 4: 80 percent / tBuOK / 1,2-dimethoxy-ethane / 12 h / 50 °C 5: 100 percent / tBuOK / dimethylsulfoxide / 0.5 h / Ambient temperature 6: 1.) 5percent SeO2 on SiO2, aq. tBuOOH, 2.) aq. H2SO4 / 1.) AcOH, 110 deg C, 1 h, 2.) 110 deg C, 1 h 7: NaBH4, CeCl3*7H2O / ethanol / 0.33 h / 0 - 20 °C 8: 0.5 h / 45 °C 9: 309 mg / H2SO4 / ethanol / 5 h / 115 °C View Scheme

1: 90 percent / Pig Liver Esterase, NaOH / dimethylsulfoxide; H2O / 3.5 h / 35 °C / pH=6.9-7.4 2: Et2NLi / tetrahydrofuran / -78 deg C -> 0 deg C 4: 100 percent / DIBAL / tetrahydrofuran / -78 °C 5: tBuOK / 1,2-dimethoxy-ethane / 12 h / 50 °C 6: tBuOK / dimethylsulfoxide / 0.5 h / Ambient temperature 7: 1.) 5percent SeO2 on SiO2, aq. tBuOOH, 2.) aq. H2SO4 / 1.) AcOH, 110 deg C, 1 h, 2.) 110 deg C, 1 h 8: 1.) NaBH4, CeCl3*7H2O / 1.) EtOH, 0 deg C -> room temperature, 20 min, 2.) 45 deg C, 30 min 9: H2SO4 / ethanol / 5 h / 115 °C View Scheme