1.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C 1.2: hexane; tetrahydrofuran / -78 - 20 °C 2.1: 897 mg / Pd(OAc)2 / acetonitrile / 1 h / Heating 3.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C 3.2: 91 percent / tetrahydrofuran; hexane / 1.5 h / -78 - 50 °C 4.1: 96 percent / hydrogen / Pd/C / ethanol / 4 h / 20 °C / 760 Torr 5.1: NaH / dimethylsulfoxide / 1 h / 0 - 20 °C 5.2: 91 percent / dimethylsulfoxide / 24 h / 75 - 80 °C 6.1: 81 percent / hydrogen; MeOH / Pd/C / triethylamine / 12 h / 20 °C / 760 Torr 7.1: 100 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C 8.1: n-BuLi / dioxane; hexane / 1 h / 20 °C 8.2: 93 percent / dioxane; hexane / 4 h / 110 °C 9.1: 54 percent / ammonium cerium(IV) nitrate / acetonitrile; H2O / 11 h / -7 - 20 °C / pH 0.7 - 1.3 View Scheme

1.1: 3.1 g / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 2.1: 87 percent / CBr4; Ph3P / CH2Cl2 / -7 °C 3.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C 3.2: 91 percent / tetrahydrofuran; hexane / 1.5 h / -78 - 50 °C 4.1: 96 percent / hydrogen / Pd/C / ethanol / 4 h / 20 °C / 760 Torr 5.1: NaH / dimethylsulfoxide / 1 h / 0 - 20 °C 5.2: 91 percent / dimethylsulfoxide / 24 h / 75 - 80 °C 6.1: 81 percent / hydrogen; MeOH / Pd/C / triethylamine / 12 h / 20 °C / 760 Torr 7.1: 100 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C 8.1: n-BuLi / dioxane; hexane / 1 h / 20 °C 8.2: 93 percent / dioxane; hexane / 4 h / 110 °C 9.1: 54 percent / ammonium cerium(IV) nitrate / acetonitrile; H2O / 11 h / -7 - 20 °C / pH 0.7 - 1.3 View Scheme

1.1: 87 percent / CBr4; Ph3P / CH2Cl2 / -7 °C 2.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C 2.2: 91 percent / tetrahydrofuran; hexane / 1.5 h / -78 - 50 °C 3.1: 96 percent / hydrogen / Pd/C / ethanol / 4 h / 20 °C / 760 Torr 4.1: NaH / dimethylsulfoxide / 1 h / 0 - 20 °C 4.2: 91 percent / dimethylsulfoxide / 24 h / 75 - 80 °C 5.1: 81 percent / hydrogen; MeOH / Pd/C / triethylamine / 12 h / 20 °C / 760 Torr 6.1: 100 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C 7.1: n-BuLi / dioxane; hexane / 1 h / 20 °C 7.2: 93 percent / dioxane; hexane / 4 h / 110 °C 8.1: 54 percent / ammonium cerium(IV) nitrate / acetonitrile; H2O / 11 h / -7 - 20 °C / pH 0.7 - 1.3 View Scheme

1.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C 1.2: 91 percent / tetrahydrofuran; hexane / 1.5 h / -78 - 50 °C 2.1: 96 percent / hydrogen / Pd/C / ethanol / 4 h / 20 °C / 760 Torr 3.1: NaH / dimethylsulfoxide / 1 h / 0 - 20 °C 3.2: 91 percent / dimethylsulfoxide / 24 h / 75 - 80 °C 4.1: 81 percent / hydrogen; MeOH / Pd/C / triethylamine / 12 h / 20 °C / 760 Torr 5.1: 100 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C 6.1: n-BuLi / dioxane; hexane / 1 h / 20 °C 6.2: 93 percent / dioxane; hexane / 4 h / 110 °C 7.1: 54 percent / ammonium cerium(IV) nitrate / acetonitrile; H2O / 11 h / -7 - 20 °C / pH 0.7 - 1.3 View Scheme

1.1: 96 percent / hydrogen / Pd/C / ethanol / 4 h / 20 °C / 760 Torr 2.1: NaH / dimethylsulfoxide / 1 h / 0 - 20 °C 2.2: 91 percent / dimethylsulfoxide / 24 h / 75 - 80 °C 3.1: 81 percent / hydrogen; MeOH / Pd/C / triethylamine / 12 h / 20 °C / 760 Torr 4.1: 100 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C 5.1: n-BuLi / dioxane; hexane / 1 h / 20 °C 5.2: 93 percent / dioxane; hexane / 4 h / 110 °C 6.1: 54 percent / ammonium cerium(IV) nitrate / acetonitrile; H2O / 11 h / -7 - 20 °C / pH 0.7 - 1.3 View Scheme

1: 75 percent / Li, NH3 2: 71 percent / dimethylsulfoxide 3: 60 percent / H2 / PtO2 / CH2Cl2 4: 95 percent / PCC / CH2Cl2 5: 82 percent / dimethylsulfoxide 6: 72 percent / cerium ammonium nitrate / acetonitrile; H2O 7: 33 percent / Pd(Ph3P)4, aq. NaHCO3 / tetrahydrofuran View Scheme

1: 60 percent / H2 / PtO2 / CH2Cl2 2: 95 percent / PCC / CH2Cl2 3: 82 percent / dimethylsulfoxide 4: 72 percent / cerium ammonium nitrate / acetonitrile; H2O 5: 33 percent / Pd(Ph3P)4, aq. NaHCO3 / tetrahydrofuran View Scheme

1: 71 percent / dimethylsulfoxide 2: 60 percent / H2 / PtO2 / CH2Cl2 3: 95 percent / PCC / CH2Cl2 4: 82 percent / dimethylsulfoxide 5: 72 percent / cerium ammonium nitrate / acetonitrile; H2O 6: 33 percent / Pd(Ph3P)4, aq. NaHCO3 / tetrahydrofuran View Scheme

tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate in tetrahydrofuran

1.1: 100 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C 2.1: n-BuLi / dioxane; hexane / 1 h / 20 °C 2.2: 93 percent / dioxane; hexane / 4 h / 110 °C 3.1: 54 percent / ammonium cerium(IV) nitrate / acetonitrile; H2O / 11 h / -7 - 20 °C / pH 0.7 - 1.3 View Scheme