1: 90 percent / pyridinium chlorochromate, NaOAc 2: 3 percent / H2SO4 / acetone; H2O / 72 h View Scheme

1: 69 percent / aq. HClO4, Tl(NO3)3*3H2O / dioxane / 0.25 h / Ambient temperature 2: 97 percent / KOH / methanol / 3 h / Ambient temperature 3: 78 percent / 1-methyl-4-piperidone, (i-PrO)3Al / toluene / 4 h / Heating 4: 96 percent / p-TsOH / diethyl ether / Ambient temperature View Scheme

1: 96 percent / KOH / methanol / 0.17 h / 50 °C 2: 77 percent / 1-methyl-4-piperidone, (i-PrO)3Al / toluene / 4 h / Heating View Scheme

1: 97 percent / KOH / methanol / 3 h / Ambient temperature 2: 78 percent / 1-methyl-4-piperidone, (i-PrO)3Al / toluene / 4 h / Heating 3: 96 percent / p-TsOH / diethyl ether / Ambient temperature View Scheme

1: H2 / 10percent Pd-C / ethanol / 0.75 h 2: 88 percent / BBr3 / 2.5 h / -30 - 0 °C View Scheme

1: 87 percent / Et3SiH, CF3CO2H / CH2Cl2 / 20 h / Ambient temperature 2: diphenyl ether / 1.5 h / Heating 3: H2 / 10percent Pd-C / ethanol / 0.75 h 4: 88 percent / BBr3 / 2.5 h / -30 - 0 °C View Scheme

1.1: 92 percent / NaBH4 / methanol / -78 - -30 °C 2.1: 80 percent / NaH; Bu4NI / tetrahydrofuran / Heating 3.1: 94 percent / HCl; MeOH 4.1: 94 percent / pyridinium chlorochromate / CH2Cl2 5.1: NaH / tetrahydrofuran 6.1: t-BuOK / tetrahydrofuran 7.1: 77 percent / 2,3-dichloro-5,6-dicyanobenzoquinone; H2O / CH2Cl2 8.1: 94 percent / pyridinium chlorochromate / CH2Cl2 9.1: 93 percent / methanol 10.1: 90 percent / Grubbs' catalyst / CH2Cl2 / Heating 11.1: 93 percent / TMS-OTf / CH2Cl2 / -78 - 0 °C 12.1: 98 percent / LiAlH4 / tetrahydrofuran 13.1: pyridinium chlorochromate / CH2Cl2 14.1: tetrahydrofuran / -78 °C 15.1: 93 percent / NaH / tetrahydrofuran 16.1: 86 percent / BuSnH; 2,2'-azobisisobutyronitrile / toluene / Heating 17.1: 98 percent / m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 18.1: 64 percent / diisobutylaluminum hydride / CH2Cl2 / -78 °C 19.1: 84 percent / pyridinium chlorochromate / CH2Cl2 20.1: p-TsOH; HOCH2CH2OH / toluene / Heating 20.2: p-TsOH; H2O / acetone / Heating 20.3: Et3SiH; CF3CO2H / benzene 21.1: 84 percent / BBr3 / CH2Cl2 / -30 - 0 °C View Scheme

1.1: 80 percent / NaH; Bu4NI / tetrahydrofuran / Heating 2.1: 94 percent / HCl; MeOH 3.1: 94 percent / pyridinium chlorochromate / CH2Cl2 4.1: NaH / tetrahydrofuran 5.1: t-BuOK / tetrahydrofuran 6.1: 77 percent / 2,3-dichloro-5,6-dicyanobenzoquinone; H2O / CH2Cl2 7.1: 94 percent / pyridinium chlorochromate / CH2Cl2 8.1: 93 percent / methanol 9.1: 90 percent / Grubbs' catalyst / CH2Cl2 / Heating 10.1: 93 percent / TMS-OTf / CH2Cl2 / -78 - 0 °C 11.1: 98 percent / LiAlH4 / tetrahydrofuran 12.1: pyridinium chlorochromate / CH2Cl2 13.1: tetrahydrofuran / -78 °C 14.1: 93 percent / NaH / tetrahydrofuran 15.1: 86 percent / BuSnH; 2,2'-azobisisobutyronitrile / toluene / Heating 16.1: 98 percent / m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 17.1: 64 percent / diisobutylaluminum hydride / CH2Cl2 / -78 °C 18.1: 84 percent / pyridinium chlorochromate / CH2Cl2 19.1: p-TsOH; HOCH2CH2OH / toluene / Heating 19.2: p-TsOH; H2O / acetone / Heating 19.3: Et3SiH; CF3CO2H / benzene 20.1: 84 percent / BBr3 / CH2Cl2 / -30 - 0 °C View Scheme

1.1: 93 percent / methanol 2.1: 90 percent / Grubbs' catalyst / CH2Cl2 / Heating 3.1: 93 percent / TMS-OTf / CH2Cl2 / -78 - 0 °C 4.1: 98 percent / LiAlH4 / tetrahydrofuran 5.1: pyridinium chlorochromate / CH2Cl2 6.1: tetrahydrofuran / -78 °C 7.1: 93 percent / NaH / tetrahydrofuran 8.1: 86 percent / BuSnH; 2,2'-azobisisobutyronitrile / toluene / Heating 9.1: 98 percent / m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 10.1: 64 percent / diisobutylaluminum hydride / CH2Cl2 / -78 °C 11.1: 84 percent / pyridinium chlorochromate / CH2Cl2 12.1: p-TsOH; HOCH2CH2OH / toluene / Heating 12.2: p-TsOH; H2O / acetone / Heating 12.3: Et3SiH; CF3CO2H / benzene 13.1: 84 percent / BBr3 / CH2Cl2 / -30 - 0 °C View Scheme

1.1: NaH / tetrahydrofuran 2.1: t-BuOK / tetrahydrofuran 3.1: 77 percent / 2,3-dichloro-5,6-dicyanobenzoquinone; H2O / CH2Cl2 4.1: 94 percent / pyridinium chlorochromate / CH2Cl2 5.1: 93 percent / methanol 6.1: 90 percent / Grubbs' catalyst / CH2Cl2 / Heating 7.1: 93 percent / TMS-OTf / CH2Cl2 / -78 - 0 °C 8.1: 98 percent / LiAlH4 / tetrahydrofuran 9.1: pyridinium chlorochromate / CH2Cl2 10.1: tetrahydrofuran / -78 °C 11.1: 93 percent / NaH / tetrahydrofuran 12.1: 86 percent / BuSnH; 2,2'-azobisisobutyronitrile / toluene / Heating 13.1: 98 percent / m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 14.1: 64 percent / diisobutylaluminum hydride / CH2Cl2 / -78 °C 15.1: 84 percent / pyridinium chlorochromate / CH2Cl2 16.1: p-TsOH; HOCH2CH2OH / toluene / Heating 16.2: p-TsOH; H2O / acetone / Heating 16.3: Et3SiH; CF3CO2H / benzene 17.1: 84 percent / BBr3 / CH2Cl2 / -30 - 0 °C View Scheme