1.1: 94 percent / pyridinium chlorochromate / CH2Cl2 2.1: NaH / tetrahydrofuran 3.1: t-BuOK / tetrahydrofuran 4.1: 77 percent / 2,3-dichloro-5,6-dicyanobenzoquinone; H2O / CH2Cl2 5.1: 94 percent / pyridinium chlorochromate / CH2Cl2 6.1: 93 percent / methanol 7.1: 90 percent / Grubbs' catalyst / CH2Cl2 / Heating 8.1: 93 percent / TMS-OTf / CH2Cl2 / -78 - 0 °C 9.1: 98 percent / LiAlH4 / tetrahydrofuran 10.1: pyridinium chlorochromate / CH2Cl2 11.1: tetrahydrofuran / -78 °C 12.1: 93 percent / NaH / tetrahydrofuran 13.1: 86 percent / BuSnH; 2,2'-azobisisobutyronitrile / toluene / Heating 14.1: 98 percent / m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 15.1: 64 percent / diisobutylaluminum hydride / CH2Cl2 / -78 °C 16.1: 84 percent / pyridinium chlorochromate / CH2Cl2 17.1: p-TsOH; HOCH2CH2OH / toluene / Heating 17.2: p-TsOH; H2O / acetone / Heating 17.3: Et3SiH; CF3CO2H / benzene 18.1: 84 percent / BBr3 / CH2Cl2 / -30 - 0 °C View Scheme

1.1: 94 percent / pyridinium chlorochromate / CH2Cl2 2.1: NaH / tetrahydrofuran 3.1: t-BuOK / tetrahydrofuran 4.1: 77 percent / 2,3-dichloro-5,6-dicyanobenzoquinone; H2O / CH2Cl2 5.1: 94 percent / pyridinium chlorochromate / CH2Cl2 6.1: 93 percent / methanol 7.1: 90 percent / Grubbs' catalyst / CH2Cl2 / Heating 8.1: 93 percent / TMS-OTf / CH2Cl2 / -78 - 0 °C 9.1: 98 percent / LiAlH4 / tetrahydrofuran 10.1: pyridinium chlorochromate / CH2Cl2 11.1: tetrahydrofuran / -78 °C 12.1: 93 percent / NaH / tetrahydrofuran 13.1: 86 percent / BuSnH; 2,2'-azobisisobutyronitrile / toluene / Heating 14.1: 98 percent / m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 15.1: 64 percent / diisobutylaluminum hydride / CH2Cl2 / -78 °C 16.1: 84 percent / pyridinium chlorochromate / CH2Cl2 17.1: p-TsOH; HOCH2CH2OH / toluene / Heating 17.2: p-TsOH; H2O / acetone / Heating 17.3: Et3SiH; CF3CO2H / benzene View Scheme