1.1: 86 percent / 4 Angstroem molecular sieves; DMTSF / CH2Cl2 / 2 h / 20 °C 2.1: 68 percent / NaBH3CN; TiCl4 / CH2Cl2; tetrahydrofuran / 1 h / -78 °C 3.1: HCl / methanol / 3 h / 55 °C 4.1: pyridine / 36 h / 20 °C 5.1: NaOMe / methanol / 0.5 h / 20 °C 6.1: 12.6 mg / imidazole / CH2Cl2; dimethylformamide / 2 h / 4 °C 7.1: NiCl2; NaBH4 / ethanol; methanol / 20 °C 7.2: SO3*Py; Et3N / dimethylsulfoxide / 1 h / 20 °C 7.3: 3.2 mg / 3HF*Et3N / tetrahydrofuran / 12 h View Scheme

1.1: 10.0 mg / Zn; aq. NH4Cl / methanol / 2 h / 20 °C 2.1: 86 percent / 4 Angstroem molecular sieves; DMTSF / CH2Cl2 / 2 h / 20 °C 3.1: 68 percent / NaBH3CN; TiCl4 / CH2Cl2; tetrahydrofuran / 1 h / -78 °C 4.1: HCl / methanol / 3 h / 55 °C 5.1: pyridine / 36 h / 20 °C 6.1: NaOMe / methanol / 0.5 h / 20 °C 7.1: 12.6 mg / imidazole / CH2Cl2; dimethylformamide / 2 h / 4 °C 8.1: NiCl2; NaBH4 / ethanol; methanol / 20 °C 8.2: SO3*Py; Et3N / dimethylsulfoxide / 1 h / 20 °C 8.3: 3.2 mg / 3HF*Et3N / tetrahydrofuran / 12 h View Scheme

1.1: 80 percent / 3HF*Et3N / tetrahydrofuran 2.1: NiCl2; NaBH4 / ethanol; methanol / 20 °C 2.2: SO3*Py; Et3N / dimethylsulfoxide / 1 h / 20 °C 2.3: 3.2 mg / 3HF*Et3N / tetrahydrofuran / 12 h View Scheme

potassium hydroxide in methanol 1 h; Ambient temperature; Yield given;

1: pyridine / 1 h / 100 °C 2: KOH / methanol / 1 h / Ambient temperature View Scheme

1: 41.4 percent / isoamyl nitrite, NaOEt / ethanol / 90 °C 2: 1.) SOCl2, 2.) aq. 1N HCl / 1.) 20 deg C, 5h, 2.) 100 deg C, 3h 3: pyridine / 1 h / 100 °C 4: KOH / methanol / 1 h / Ambient temperature View Scheme

1: 1.) SOCl2, 2.) aq. 1N HCl / 1.) 20 deg C, 5h, 2.) 100 deg C, 3h 2: pyridine / 1 h / 100 °C 3: KOH / methanol / 1 h / Ambient temperature View Scheme