1: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 2: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 3: NaBH4 / methanol / 24 h / 20 °C View Scheme

1: MCPBA / CHCl3 2: FeSO4*7H2O / methanol View Scheme

1.1: 96 percent / pyridinium chlorochromate / tetrahydrofuran / 3 h / 20 °C 2.1: dioxane / 24 h / 20 °C 2.2: 64 percent / HCl / dioxane / 24 h / 20 °C 3.1: 94 percent / pyridine / 0.25 h / 0 °C 4.1: 61 percent / phenyliodine(III) bis(trifluoroacetate) / 2,2,2-trifluoro-ethanol / 0.17 h / -40 °C 5.1: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 6.1: 83 percent / pyridine / 3 h / 0 °C 7.1: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 8.1: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 9.1: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 10.1: NaBH4 / methanol / 24 h / 20 °C View Scheme

1.1: K2CO3 / dimethylformamide / 1 h / 85 °C 1.2: 76 percent / dimethylformamide / 24 h / 20 °C 2.1: 95 percent / K2CO3 / dimethylformamide / 1.5 h / 150 °C 3.1: 96 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / 60 °C 4.1: 96 percent / pyridinium chlorochromate / tetrahydrofuran / 3 h / 20 °C 5.1: dioxane / 24 h / 20 °C 5.2: 64 percent / HCl / dioxane / 24 h / 20 °C 6.1: 94 percent / pyridine / 0.25 h / 0 °C 7.1: 61 percent / phenyliodine(III) bis(trifluoroacetate) / 2,2,2-trifluoro-ethanol / 0.17 h / -40 °C 8.1: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 9.1: 83 percent / pyridine / 3 h / 0 °C 10.1: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 11.1: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 12.1: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 13.1: NaBH4 / methanol / 24 h / 20 °C View Scheme

1.1: dioxane / 24 h / 20 °C 1.2: 64 percent / HCl / dioxane / 24 h / 20 °C 2.1: 94 percent / pyridine / 0.25 h / 0 °C 3.1: 61 percent / phenyliodine(III) bis(trifluoroacetate) / 2,2,2-trifluoro-ethanol / 0.17 h / -40 °C 4.1: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 5.1: 83 percent / pyridine / 3 h / 0 °C 6.1: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 7.1: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 8.1: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 9.1: NaBH4 / methanol / 24 h / 20 °C View Scheme

1.1: 95 percent / K2CO3 / dimethylformamide / 1.5 h / 150 °C 2.1: 96 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / 60 °C 3.1: 96 percent / pyridinium chlorochromate / tetrahydrofuran / 3 h / 20 °C 4.1: dioxane / 24 h / 20 °C 4.2: 64 percent / HCl / dioxane / 24 h / 20 °C 5.1: 94 percent / pyridine / 0.25 h / 0 °C 6.1: 61 percent / phenyliodine(III) bis(trifluoroacetate) / 2,2,2-trifluoro-ethanol / 0.17 h / -40 °C 7.1: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 8.1: 83 percent / pyridine / 3 h / 0 °C 9.1: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 10.1: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 11.1: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 12.1: NaBH4 / methanol / 24 h / 20 °C View Scheme

1.1: 96 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / 60 °C 2.1: 96 percent / pyridinium chlorochromate / tetrahydrofuran / 3 h / 20 °C 3.1: dioxane / 24 h / 20 °C 3.2: 64 percent / HCl / dioxane / 24 h / 20 °C 4.1: 94 percent / pyridine / 0.25 h / 0 °C 5.1: 61 percent / phenyliodine(III) bis(trifluoroacetate) / 2,2,2-trifluoro-ethanol / 0.17 h / -40 °C 6.1: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 7.1: 83 percent / pyridine / 3 h / 0 °C 8.1: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 9.1: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 10.1: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 11.1: NaBH4 / methanol / 24 h / 20 °C View Scheme

iron(II) sulfate in methanol

1: 46.3 mg / 48 h / Heating 2: 94 percent / lithium aluminum hydride / tetrahydrofuran / 7 h / 20 °C View Scheme