1: 1.) NaOH, 2.) NaIO4 / 1.) H2O, 40 deg C, 0.5 h, 2.) H2O, 0.5 h 2: 93 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 2.5 h / Ambient temperature 3: 1.) nBuLi / 1.) THF, -78 deg C, 0.5 h, 2.) THF, from -78 deg C t0 -20 deg C, 2.5 h View Scheme

1: pyridine / 2 h / 0 °C 2: water; potassium hydroxide / 6 h / 25 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C 1.2: 78 percent / tetrahydrofuran; hexane / -78 - 20 °C 2.1: 92 percent / sodium hydride / dimethylformamide / 0.5 h / 0 °C View Scheme

1: 95 percent / NaH / dimethylformamide 2: 7.5 percent / P(NMe2)3 / CH2Cl2 3: 54 percent / 4-chloroperoxybenzoic acid; hydroquinone / CH2Cl2 / 16 h / 20 °C 4: 95 percent / NaN3 / dimethylformamide / 5 h / 20 °C 5: tetrahydrofuran / 2 h / 24 °C 6: 904 mg / tetrahydrofuran / 72 h / 20 °C 7: 100 percent / HCl; water / tetrahydrofuran / 0.67 h / 20 °C 8: 97 percent / ammonium cerium(IV) nitrate / acetonitrile; H2O / 0.33 h / 20 °C 9: 99 percent / NH3 / methanol / 4 h / 37 °C 10: 100 percent / H2 / Pd/C / ethyl acetate / 0.5 h / 20 °C 11: 100 percent / CF3COOH; water / 2 h / 0 °C View Scheme

1: 1.) NaH / 1.) THF, 0 deg C, 15 min, 2.) RT, overnight 2: 1.) n-BuLi / 1.) THF, hexane, -70 deg C, 0.5 h, 2.) from -70 deg C to RT, 2 h 3: 95 percent / CH3ONa / methanol / 24 h / Ambient temperature 4: 80 percent / CrO3, pyridine / CH2Cl2 / 1 h / 14 - 25 °C 5: 42 percent / K2CO3, 18-crown-6 / benzene / 0.67 h / 56 °C 6: 97 percent / NaBH4, CeCl3*7H2O / methanol / 0.17 h / 0 - 5 °C 7: 100 percent / Et3N / CH2Cl2 / 0.17 h / -5 - 0 °C 8: 74 percent / LiN3, P(NMe2)3 / dimethylsulfoxide / Ambient temperature 9: H2 / Lindlar's catalyst / butan-1-ol / 3 h / 760 Torr 10: Et3N / butan-1-ol / 20 h / Heating 11: conc. HCl / 42 h / Ambient temperature 12: 70 percent / liquid NH3 / methanol / 18 h / 60 °C 13: 50 percent / 1 M BCl3 / CH2Cl2; hexane / 2.5 h / -75 °C View Scheme

1: 82 percent / imidazole / dimethylformamide / 2.5 h / 60 °C 2: 72 percent / 80percent aq. AcOH / 1.5 h / Heating 3: 96 percent / acetone / 2.5 h / Heating 4: 96 percent / Raney Ni / tetrahydrofuran / 2.5 h / Heating View Scheme