1: 89 percent / dppp; 1,8-diazabicyclo[5.4.0]undec-7-ene / Pd2(dba)3 / dimethylsulfoxide / 4 h / 50 °C 2: ethylenediamine / 6 h / 160 °C 3: CH2Cl2 / 12 h / 20 °C 4: H2 / Rh(acac)(CO)2; biphephos / tetrahydrofuran / 8 h / 65 °C / 3800 Torr 5: 10-camphorsulfonic acid / tetrahydrofuran / 9 h / 20 °C 6: 100 percent / H2 / palladium on carbon / ethanol / 12 h / 20 °C / 760 Torr 7: 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 6 h / 20 °C 8: 96 percent / sodium; naphthalene / tetrahydrofuran / 1 h / -78 °C 9: 87 percent / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide / 18 h / 0 °C 10: 95 percent / trifluoroacetic acid; NaHCO3 / 2 h / 20 °C View Scheme

1: tetrahydrofuran / 20 °C 2: 220 mg / BH3*Me2S / tetrahydrofuran / 24 h / 55 °C 3: tetrahydrofuran / 20 °C 4: sodium borohydride / methanol / 3 h 5: 96 percent / hydrogen chloride / methanol / 20 °C View Scheme

1: 220 mg / BH3*Me2S / tetrahydrofuran / 24 h / 55 °C 2: tetrahydrofuran / 20 °C 3: sodium borohydride / methanol / 3 h 4: 96 percent / hydrogen chloride / methanol / 20 °C View Scheme

1: 83 percent / bromocresol green; HCl; NaBH3CN / methanol / 16 h / 20 °C / pH 5 2: 88 percent / conc. HCl / methanol / 4 h View Scheme

1: 27.8 mg / BH3*THF / tetrahydrofuran / 4 h / 45 °C 2: 83 percent / bromocresol green; HCl; NaBH3CN / methanol / 16 h / 20 °C / pH 5 3: 88 percent / conc. HCl / methanol / 4 h View Scheme

1: 87 percent / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide / 18 h / 0 °C 2: 95 percent / trifluoroacetic acid; NaHCO3 / 2 h / 20 °C View Scheme

1: 96 percent / sodium; naphthalene / tetrahydrofuran / 1 h / -78 °C 2: 87 percent / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide / 18 h / 0 °C 3: 95 percent / trifluoroacetic acid; NaHCO3 / 2 h / 20 °C View Scheme

1.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 4 h / 20 °C 2.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 3.1: sodium azide / N,N-dimethyl-formamide / 4 h / 80 °C / Inert atmosphere 4.1: palladium 10 on activated carbon; hydrogen; potassium carbonate / methanol / 4 h / 20 °C 5.1: borane-THF / 5 h / Inert atmosphere; Reflux 5.2: 0.5 h / 0 - 20 °C / Inert atmosphere 6.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / Inert atmosphere 7.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere 8.1: pyridine / ethanol / 0.5 h / 20 °C / Inert atmosphere 9.1: borane-THF / tetrahydrofuran / 4 h / 50 °C / Inert atmosphere 10.1: sodium tetrahydroborate / methanol / Inert atmosphere 11.1: hydrogenchloride / methanol; water / Inert atmosphere View Scheme

1.1: C28H23F6N3O2 / dichloromethane / 192 h / 20 °C / Inert atmosphere 2.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 4 h / 20 °C 3.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 4.1: sodium azide / N,N-dimethyl-formamide / 4 h / 80 °C / Inert atmosphere 5.1: palladium 10 on activated carbon; hydrogen; potassium carbonate / methanol / 4 h / 20 °C 6.1: borane-THF / 5 h / Inert atmosphere; Reflux 6.2: 0.5 h / 0 - 20 °C / Inert atmosphere 7.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / Inert atmosphere 8.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere 9.1: pyridine / ethanol / 0.5 h / 20 °C / Inert atmosphere 10.1: borane-THF / tetrahydrofuran / 4 h / 50 °C / Inert atmosphere 11.1: sodium tetrahydroborate / methanol / Inert atmosphere 12.1: hydrogenchloride / methanol; water / Inert atmosphere View Scheme

1.1: (S)-ALB; KO-t-Bu / tetrahydrofuran; CH2Cl2 / -40 °C 2.1: 100 percent / HF; pyridine / tetrahydrofuran / 0 - 20 °C 3.1: Dess-Martin periodinane / CH2Cl2 / 14 h / 20 °C 4.1: TMSCl; DBU / CH2Cl2 / 1 h / 0 °C 4.2: 83 percent / AcOH / 0.25 h / -78 °C 5.1: 85 percent / Zn dust; NH4Cl / aq. methanol / 20 °C 6.1: 81 percent / NaBH3CN; MS 3A / methanol / 3 h / 20 °C 7.1: 30 percent / LiAlH4 / tetrahydrofuran / 20 °C View Scheme