1.1: 5.50 mg / NaBH4 / ethanol / 3 h / 0 °C 2.1: 4.9 mg / NaOH; NaHSO3 / ethanol / 4 h / 70 - 80 °C 3.1: 74 percent / HBr; AcOH / 16 h / 20 °C 4.1: Li; NH3 / tetrahydrofuran; H2O / 0.75 h / -78 - -33 °C 4.2: 76 percent / tetrahydrofuran; H2O / 2 h / Heating 5.1: 98 percent / KOtBu / toluene / 4 h / Heating 6.1: 100 percent / HCl / tetrahydrofuran / 12 h / 20 °C 7.1: 89 percent / H2; Et3N / 10percent Pd/C / methanol / 12 h / 20 °C 8.1: 98 percent / KOtBu / toluene / 3 h / Heating 9.1: 26 percent / AgO; HNO3 / dioxane / 20 °C View Scheme

1.1: 4.9 mg / NaOH; NaHSO3 / ethanol / 4 h / 70 - 80 °C 2.1: 74 percent / HBr; AcOH / 16 h / 20 °C 3.1: Li; NH3 / tetrahydrofuran; H2O / 0.75 h / -78 - -33 °C 3.2: 76 percent / tetrahydrofuran; H2O / 2 h / Heating 4.1: 98 percent / KOtBu / toluene / 4 h / Heating 5.1: 100 percent / HCl / tetrahydrofuran / 12 h / 20 °C 6.1: 89 percent / H2; Et3N / 10percent Pd/C / methanol / 12 h / 20 °C 7.1: 98 percent / KOtBu / toluene / 3 h / Heating 8.1: 26 percent / AgO; HNO3 / dioxane / 20 °C View Scheme

1.1: 96 percent / H2SO4 / methanol 2.1: 5.50 mg / NaBH4 / ethanol / 3 h / 0 °C 3.1: 4.9 mg / NaOH; NaHSO3 / ethanol / 4 h / 70 - 80 °C 4.1: 74 percent / HBr; AcOH / 16 h / 20 °C 5.1: Li; NH3 / tetrahydrofuran; H2O / 0.75 h / -78 - -33 °C 5.2: 76 percent / tetrahydrofuran; H2O / 2 h / Heating 6.1: 98 percent / KOtBu / toluene / 4 h / Heating 7.1: 100 percent / HCl / tetrahydrofuran / 12 h / 20 °C 8.1: 89 percent / H2; Et3N / 10percent Pd/C / methanol / 12 h / 20 °C 9.1: 98 percent / KOtBu / toluene / 3 h / Heating 10.1: 26 percent / AgO; HNO3 / dioxane / 20 °C View Scheme

1.1: PbO2 / 20 - 22 °C 2.1: 96 percent / H2SO4 / methanol 3.1: 5.50 mg / NaBH4 / ethanol / 3 h / 0 °C 4.1: 4.9 mg / NaOH; NaHSO3 / ethanol / 4 h / 70 - 80 °C 5.1: 74 percent / HBr; AcOH / 16 h / 20 °C 6.1: Li; NH3 / tetrahydrofuran; H2O / 0.75 h / -78 - -33 °C 6.2: 76 percent / tetrahydrofuran; H2O / 2 h / Heating 7.1: 98 percent / KOtBu / toluene / 4 h / Heating 8.1: 100 percent / HCl / tetrahydrofuran / 12 h / 20 °C 9.1: 89 percent / H2; Et3N / 10percent Pd/C / methanol / 12 h / 20 °C 10.1: 98 percent / KOtBu / toluene / 3 h / Heating 11.1: 26 percent / AgO; HNO3 / dioxane / 20 °C View Scheme

1: 89 percent / H2; Et3N / 10percent Pd/C / methanol / 12 h / 20 °C 2: 98 percent / KOtBu / toluene / 3 h / Heating 3: 26 percent / AgO; HNO3 / dioxane / 20 °C View Scheme

ammonium cerium(IV) nitrate in water; acetonitrile T=-7 - 20°C; Oxidation; pH=0.7 - 1.3; 11 h;

1: 98 percent / KOtBu / toluene / 3 h / Heating 2: 26 percent / AgO; HNO3 / dioxane / 20 °C View Scheme

1: 40 percent / AgO; HNO3 / dioxane / 20 °C 2: 96 percent / H2SO4 / methanol View Scheme

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: 10 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: 10 percent / ammonium cerium(IV) nitrate / acetonitrile; H2O / 11 h / -7 - 20 °C / pH 0.7 - 1.3 View Scheme