1.1: 94 percent / pyridinium chlorochromate / CH2Cl2 2.1: 93 percent / methanol 3.1: 90 percent / Grubbs' catalyst / CH2Cl2 / Heating 4.1: 93 percent / TMS-OTf / CH2Cl2 / -78 - 0 °C 5.1: 98 percent / LiAlH4 / tetrahydrofuran 6.1: pyridinium chlorochromate / CH2Cl2 7.1: tetrahydrofuran / -78 °C 8.1: 93 percent / NaH / tetrahydrofuran 9.1: 86 percent / BuSnH; 2,2'-azobisisobutyronitrile / toluene / Heating 10.1: 98 percent / m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 11.1: 64 percent / diisobutylaluminum hydride / CH2Cl2 / -78 °C 12.1: 84 percent / pyridinium chlorochromate / CH2Cl2 13.1: p-TsOH; HOCH2CH2OH / toluene / Heating 13.2: p-TsOH; H2O / acetone / Heating 13.3: Et3SiH; CF3CO2H / benzene 14.1: 84 percent / BBr3 / CH2Cl2 / -30 - 0 °C View Scheme

1.1: 94 percent / pyridinium chlorochromate / CH2Cl2 2.1: 93 percent / methanol 3.1: 90 percent / Grubbs' catalyst / CH2Cl2 / Heating 4.1: 93 percent / TMS-OTf / CH2Cl2 / -78 - 0 °C 5.1: 98 percent / LiAlH4 / tetrahydrofuran 6.1: pyridinium chlorochromate / CH2Cl2 7.1: tetrahydrofuran / -78 °C 8.1: 93 percent / NaH / tetrahydrofuran 9.1: 86 percent / BuSnH; 2,2'-azobisisobutyronitrile / toluene / Heating 10.1: 98 percent / m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 11.1: 64 percent / diisobutylaluminum hydride / CH2Cl2 / -78 °C 12.1: 84 percent / pyridinium chlorochromate / CH2Cl2 13.1: p-TsOH; HOCH2CH2OH / toluene / Heating 13.2: p-TsOH; H2O / acetone / Heating 13.3: Et3SiH; CF3CO2H / benzene View Scheme