1.1: NaOMe / methanol; tetrahydrofuran; CH2Cl2 / 3 h / 20 °C 1.2: 78 percent / t-BuOK / dimethylformamide; tetrahydrofuran / 6 h / 0 - 20 °C 2.1: 3.70 g / NH4Cl; NaN3 / dimethylformamide; H2O / 2 h / 80 °C 3.1: 3.84 g / n-tetrabutylammonium iodide; NaH / dimethylformamide / 2.5 h / 0 °C 4.1: 50 percent / 3 percent HCl / 18 h / 20 °C 5.1: 44.1 g / pyridine / CH2Cl2 / 1.6 h / -60 °C 6.1: PPh3 / CH2Cl2 / 4 h / 20 - 45 °C 6.2: K2CO3 / H2O; tetrahydrofuran; methanol / 96 h / 20 °C 6.3: 27.3 g / tetrahydrofuran; methanol; H2O / 7 h / 0 °C 7.1: TFA / dioxane; H2O / 11 h / 20 °C 7.2: 71 percent / NaBH4 / ethanol / 2 h / 0 °C 8.1: imidazole / dimethylformamide / 1 h / 20 °C 9.1: 3.76 g / tetrabutylammonium iodide; NaH / dimethylformamide / 3 h / 0 °C 10.1: 72 percent / sodium acetate / PdCl2 / acetic acid; H2O / 3.5 h / 50 °C 11.1: 87 percent / AcOH; TBAF / tetrahydrofuran / 8 h / 20 °C 12.1: H2 / 10 percent Pd/C / acetic acid; ethanol; H2O / 45 h / 20 °C 12.2: 53 percent / HCl / H2O View Scheme

1.1: NaOMe / methanol; tetrahydrofuran; CH2Cl2 / 3 h / 20 °C 1.2: 78 percent / t-BuOK / dimethylformamide; tetrahydrofuran / 6 h / 0 - 20 °C 2.1: 3.70 g / NH4Cl; NaN3 / dimethylformamide; H2O / 2 h / 80 °C 3.1: 3.84 g / n-tetrabutylammonium iodide; NaH / dimethylformamide / 2.5 h / 0 °C 4.1: 50 percent / 3 percent HCl / 18 h / 20 °C 5.1: 44.1 g / pyridine / CH2Cl2 / 1.6 h / -60 °C 6.1: PPh3 / CH2Cl2 / 4 h / 20 - 45 °C 6.2: K2CO3 / H2O; tetrahydrofuran; methanol / 96 h / 20 °C 6.3: 27.3 g / tetrahydrofuran; methanol; H2O / 7 h / 0 °C 7.1: TFA / dioxane; H2O / 11 h / 20 °C 7.2: 71 percent / NaBH4 / ethanol / 2 h / 0 °C 8.1: imidazole / dimethylformamide / 1 h / 20 °C 9.1: 3.76 g / tetrabutylammonium iodide; NaH / dimethylformamide / 3 h / 0 °C 10.1: 72 percent / sodium acetate / PdCl2 / acetic acid; H2O / 3.5 h / 50 °C 11.1: 87 percent / AcOH; TBAF / tetrahydrofuran / 8 h / 20 °C 12.1: H2 / 10 percent Pd/C / acetic acid; ethanol; H2O / 45 h / 20 °C 12.2: 53 percent / HCl / H2O View Scheme