1: With sodium tetrahydroborate; nickel dichloride in methanol; ethanol T=20°C; 2: With pyridine-SO3 complex; triethylamine in dimethyl sulfoxide T=20°C; 1 h; 3: With triethylamine tris(hydrogen fluoride) in tetrahydrofuran 12 h; Further stages.;

1.1: 100 percent / Pd2(dba)3*CHCl3; Ph3As; CuI / dimethylformamide / 48 h / 20 °C 2.1: 100 percent / N,N-diisopropylethylamine / CH2Cl2 / 24 h / 20 °C 3.1: 100 percent / 3HF*Et3N / tetrahydrofuran / 50 h / 20 °C 4.1: N,N-diisoropylethylamine / CH2Cl2 / 0.5 h / -78 °C 5.1: N,N-diisoropylethylamine / CH2Cl2 / 1 h / -78 °C 6.1: 10.0 mg / Zn; aq. NH4Cl / methanol / 2 h / 20 °C 7.1: 86 percent / 4 Angstroem molecular sieves; DMTSF / CH2Cl2 / 2 h / 20 °C 8.1: 68 percent / NaBH3CN; TiCl4 / CH2Cl2; tetrahydrofuran / 1 h / -78 °C 9.1: HCl / methanol / 3 h / 55 °C 10.1: pyridine / 36 h / 20 °C 11.1: NaOMe / methanol / 0.5 h / 20 °C 12.1: 12.6 mg / imidazole / CH2Cl2; dimethylformamide / 2 h / 4 °C 13.1: NiCl2; NaBH4 / ethanol; methanol / 20 °C 13.2: SO3*Py; Et3N / dimethylsulfoxide / 1 h / 20 °C 13.3: 3.2 mg / 3HF*Et3N / tetrahydrofuran / 12 h View Scheme

1.1: 89 percent / I2; DMAP / CH2Cl2 / 5 h / 20 °C 2.1: 100 percent / Pd2(dba)3*CHCl3; Ph3As; CuI / dimethylformamide / 48 h / 20 °C 3.1: 100 percent / N,N-diisopropylethylamine / CH2Cl2 / 24 h / 20 °C 4.1: 100 percent / 3HF*Et3N / tetrahydrofuran / 50 h / 20 °C 5.1: N,N-diisoropylethylamine / CH2Cl2 / 0.5 h / -78 °C 6.1: N,N-diisoropylethylamine / CH2Cl2 / 1 h / -78 °C 7.1: 10.0 mg / Zn; aq. NH4Cl / methanol / 2 h / 20 °C 8.1: 86 percent / 4 Angstroem molecular sieves; DMTSF / CH2Cl2 / 2 h / 20 °C 9.1: 68 percent / NaBH3CN; TiCl4 / CH2Cl2; tetrahydrofuran / 1 h / -78 °C 10.1: HCl / methanol / 3 h / 55 °C 11.1: pyridine / 36 h / 20 °C 12.1: NaOMe / methanol / 0.5 h / 20 °C 13.1: 12.6 mg / imidazole / CH2Cl2; dimethylformamide / 2 h / 4 °C 14.1: NiCl2; NaBH4 / ethanol; methanol / 20 °C 14.2: SO3*Py; Et3N / dimethylsulfoxide / 1 h / 20 °C 14.3: 3.2 mg / 3HF*Et3N / tetrahydrofuran / 12 h View Scheme

1.1: 89 percent / I2; DMAP / CH2Cl2 / 5 h / 20 °C 2.1: 100 percent / Pd2(dba)3*CHCl3; Ph3As; CuI / dimethylformamide / 48 h / 20 °C 3.1: 100 percent / N,N-diisopropylethylamine / CH2Cl2 / 24 h / 20 °C 4.1: 100 percent / 3HF*Et3N / tetrahydrofuran / 50 h / 20 °C 5.1: N,N-diisoropylethylamine / CH2Cl2 / 0.5 h / -78 °C 6.1: N,N-diisoropylethylamine / CH2Cl2 / 1 h / -78 °C 7.1: 10.0 mg / Zn; aq. NH4Cl / methanol / 2 h / 20 °C 8.1: 86 percent / 4 Angstroem molecular sieves; DMTSF / CH2Cl2 / 2 h / 20 °C 9.1: 68 percent / NaBH3CN; TiCl4 / CH2Cl2; tetrahydrofuran / 1 h / -78 °C 10.1: HCl / methanol / 3 h / 55 °C 11.1: pyridine / 36 h / 20 °C 12.1: NaOMe / methanol / 0.5 h / 20 °C 13.1: 12.6 mg / imidazole / CH2Cl2; dimethylformamide / 2 h / 4 °C 14.1: NiCl2; NaBH4 / ethanol; methanol / 20 °C 14.2: SO3*Py; Et3N / dimethylsulfoxide / 1 h / 20 °C 14.3: 3.2 mg / 3HF*Et3N / tetrahydrofuran / 12 h View Scheme

1.1: 100 percent / Pd2(dba)3*CHCl3; Ph3As; CuI / dimethylformamide / 48 h / 20 °C 2.1: 100 percent / N,N-diisopropylethylamine / CH2Cl2 / 24 h / 20 °C 3.1: 100 percent / 3HF*Et3N / tetrahydrofuran / 50 h / 20 °C 4.1: N,N-diisoropylethylamine / CH2Cl2 / 0.5 h / -78 °C 5.1: N,N-diisoropylethylamine / CH2Cl2 / 1 h / -78 °C 6.1: 10.0 mg / Zn; aq. NH4Cl / methanol / 2 h / 20 °C 7.1: 86 percent / 4 Angstroem molecular sieves; DMTSF / CH2Cl2 / 2 h / 20 °C 8.1: 68 percent / NaBH3CN; TiCl4 / CH2Cl2; tetrahydrofuran / 1 h / -78 °C 9.1: HCl / methanol / 3 h / 55 °C 10.1: pyridine / 36 h / 20 °C 11.1: NaOMe / methanol / 0.5 h / 20 °C 12.1: 12.6 mg / imidazole / CH2Cl2; dimethylformamide / 2 h / 4 °C 13.1: NiCl2; NaBH4 / ethanol; methanol / 20 °C 13.2: SO3*Py; Et3N / dimethylsulfoxide / 1 h / 20 °C 13.3: 3.2 mg / 3HF*Et3N / tetrahydrofuran / 12 h View Scheme

1.1: N,N-diisoropylethylamine / CH2Cl2 / 0.5 h / -78 °C 2.1: N,N-diisoropylethylamine / CH2Cl2 / 1 h / -78 °C 3.1: 10.0 mg / Zn; aq. NH4Cl / methanol / 2 h / 20 °C 4.1: 86 percent / 4 Angstroem molecular sieves; DMTSF / CH2Cl2 / 2 h / 20 °C 5.1: 68 percent / NaBH3CN; TiCl4 / CH2Cl2; tetrahydrofuran / 1 h / -78 °C 6.1: HCl / methanol / 3 h / 55 °C 7.1: pyridine / 36 h / 20 °C 8.1: NaOMe / methanol / 0.5 h / 20 °C 9.1: 12.6 mg / imidazole / CH2Cl2; dimethylformamide / 2 h / 4 °C 10.1: NiCl2; NaBH4 / ethanol; methanol / 20 °C 10.2: SO3*Py; Et3N / dimethylsulfoxide / 1 h / 20 °C 10.3: 3.2 mg / 3HF*Et3N / tetrahydrofuran / 12 h View Scheme

1.1: 100 percent / N,N-diisopropylethylamine / CH2Cl2 / 24 h / 20 °C 2.1: 100 percent / 3HF*Et3N / tetrahydrofuran / 50 h / 20 °C 3.1: N,N-diisoropylethylamine / CH2Cl2 / 0.5 h / -78 °C 4.1: N,N-diisoropylethylamine / CH2Cl2 / 1 h / -78 °C 5.1: 10.0 mg / Zn; aq. NH4Cl / methanol / 2 h / 20 °C 6.1: 86 percent / 4 Angstroem molecular sieves; DMTSF / CH2Cl2 / 2 h / 20 °C 7.1: 68 percent / NaBH3CN; TiCl4 / CH2Cl2; tetrahydrofuran / 1 h / -78 °C 8.1: HCl / methanol / 3 h / 55 °C 9.1: pyridine / 36 h / 20 °C 10.1: NaOMe / methanol / 0.5 h / 20 °C 11.1: 12.6 mg / imidazole / CH2Cl2; dimethylformamide / 2 h / 4 °C 12.1: NiCl2; NaBH4 / ethanol; methanol / 20 °C 12.2: SO3*Py; Et3N / dimethylsulfoxide / 1 h / 20 °C 12.3: 3.2 mg / 3HF*Et3N / tetrahydrofuran / 12 h View Scheme

1.1: 68 percent / NaBH3CN; TiCl4 / CH2Cl2; tetrahydrofuran / 1 h / -78 °C 2.1: HCl / methanol / 3 h / 55 °C 3.1: pyridine / 36 h / 20 °C 4.1: NaOMe / methanol / 0.5 h / 20 °C 5.1: 12.6 mg / imidazole / CH2Cl2; dimethylformamide / 2 h / 4 °C 6.1: NiCl2; NaBH4 / ethanol; methanol / 20 °C 6.2: SO3*Py; Et3N / dimethylsulfoxide / 1 h / 20 °C 6.3: 3.2 mg / 3HF*Et3N / tetrahydrofuran / 12 h View Scheme

1.1: HCl / methanol / 3 h / 55 °C 2.1: pyridine / 36 h / 20 °C 3.1: NaOMe / methanol / 0.5 h / 20 °C 4.1: 12.6 mg / imidazole / CH2Cl2; dimethylformamide / 2 h / 4 °C 5.1: NiCl2; NaBH4 / ethanol; methanol / 20 °C 5.2: SO3*Py; Et3N / dimethylsulfoxide / 1 h / 20 °C 5.3: 3.2 mg / 3HF*Et3N / tetrahydrofuran / 12 h View Scheme

1.1: 100 percent / 3HF*Et3N / tetrahydrofuran / 50 h / 20 °C 2.1: N,N-diisoropylethylamine / CH2Cl2 / 0.5 h / -78 °C 3.1: N,N-diisoropylethylamine / CH2Cl2 / 1 h / -78 °C 4.1: 10.0 mg / Zn; aq. NH4Cl / methanol / 2 h / 20 °C 5.1: 86 percent / 4 Angstroem molecular sieves; DMTSF / CH2Cl2 / 2 h / 20 °C 6.1: 68 percent / NaBH3CN; TiCl4 / CH2Cl2; tetrahydrofuran / 1 h / -78 °C 7.1: HCl / methanol / 3 h / 55 °C 8.1: pyridine / 36 h / 20 °C 9.1: NaOMe / methanol / 0.5 h / 20 °C 10.1: 12.6 mg / imidazole / CH2Cl2; dimethylformamide / 2 h / 4 °C 11.1: NiCl2; NaBH4 / ethanol; methanol / 20 °C 11.2: SO3*Py; Et3N / dimethylsulfoxide / 1 h / 20 °C 11.3: 3.2 mg / 3HF*Et3N / tetrahydrofuran / 12 h View Scheme