palladium 10 on activated carbon; hydrogen; triethylamine in ethyl acetate 4 h;

1: 98 percent / H2, NaOH / 10percent Pd/C / H2O / 12 h / 22501.8 Torr 2: 98 percent / conc.H2SO4 / Heating 3: 1) NaH, 2) tetrabutylammonium iodide / 1) THF, 0 deg C, 0.5 h, 2) 0 deg C 4: 95 percent / LiAlH4 / diethyl ether / 0 °C 5: 81 percent / CrO3, pyridine / CH2Cl2 / Ambient temperature 6: 80 percent / BF3*OEt2 / CH2Cl2 / 1.5 h / 0 °C 8: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 9: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 10: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 11: 1) CuCN / 1) ether, -78 to -40 deg C, 2) ether, -78 to -20 deg C, then 2 h 12: 58 percent / MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 13: 90 percent / p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 99 percent / methanol / Heating 2: 98 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, -78 deg C, 1 h, 2) -50 deg C 4: DIBAL / tetrahydrofuran; toluene / 2 h / -78 °C 5: 1) Zn-powder, 2) trimethylsilyl chloride / 1) THF, r.t., 15 min, 2) r.t., 45 min 6: 1) Me3OBF4, 2) aq.Na2CO3 / 1) CH2Cl2, r.t., 2 h, 2) 6 h 8: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 9: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 10: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 11: 1) CuCN / 1) ether, -78 to -40 deg C, 2) ether, -78 to -20 deg C, then 2 h 12: 58 percent / MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 13: 90 percent / p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 98 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1) lithium diisopropylamide / 1) THF, -78 deg C, 1 h, 2) -50 deg C 3: DIBAL / tetrahydrofuran; toluene / 2 h / -78 °C 4: 1) Zn-powder, 2) trimethylsilyl chloride / 1) THF, r.t., 15 min, 2) r.t., 45 min 5: 1) Me3OBF4, 2) aq.Na2CO3 / 1) CH2Cl2, r.t., 2 h, 2) 6 h 7: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 8: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 9: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 10: 1) CuCN / 1) ether, -78 to -40 deg C, 2) ether, -78 to -20 deg C, then 2 h 11: 58 percent / MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 12: 90 percent / p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 98 percent / conc.H2SO4 / Heating 2: 1) NaH, 2) tetrabutylammonium iodide / 1) THF, 0 deg C, 0.5 h, 2) 0 deg C 3: 95 percent / LiAlH4 / diethyl ether / 0 °C 4: 81 percent / CrO3, pyridine / CH2Cl2 / Ambient temperature 5: 80 percent / BF3*OEt2 / CH2Cl2 / 1.5 h / 0 °C 7: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 8: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 9: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 10: 1) CuCN / 1) ether, -78 to -40 deg C, 2) ether, -78 to -20 deg C, then 2 h 11: 58 percent / MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 12: 90 percent / p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 81 percent / CrO3, pyridine / CH2Cl2 / Ambient temperature 2: 80 percent / BF3*OEt2 / CH2Cl2 / 1.5 h / 0 °C 4: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 5: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 6: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 7: 1) CuCN / 1) ether, -78 to -40 deg C, 2) ether, -78 to -20 deg C, then 2 h 8: 58 percent / MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 9: 90 percent / p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 95 percent / LiAlH4 / diethyl ether / 0 °C 2: 81 percent / CrO3, pyridine / CH2Cl2 / Ambient temperature 3: 80 percent / BF3*OEt2 / CH2Cl2 / 1.5 h / 0 °C 5: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 6: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 7: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 8: 1) CuCN / 1) ether, -78 to -40 deg C, 2) ether, -78 to -20 deg C, then 2 h 9: 58 percent / MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 10: 90 percent / p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 1) NaH, 2) tetrabutylammonium iodide / 1) THF, 0 deg C, 0.5 h, 2) 0 deg C 2: 95 percent / LiAlH4 / diethyl ether / 0 °C 3: 81 percent / CrO3, pyridine / CH2Cl2 / Ambient temperature 4: 80 percent / BF3*OEt2 / CH2Cl2 / 1.5 h / 0 °C 6: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 7: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 8: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 9: 1) CuCN / 1) ether, -78 to -40 deg C, 2) ether, -78 to -20 deg C, then 2 h 10: 58 percent / MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 11: 90 percent / p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 80 percent / BF3*OEt2 / CH2Cl2 / 1.5 h / 0 °C 3: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 4: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 5: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 6: 1) CuCN / 1) ether, -78 to -40 deg C, 2) ether, -78 to -20 deg C, then 2 h 7: 58 percent / MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 8: 90 percent / p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

2: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 3: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 4: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 5: 1) CuCN / 1) ether, -78 to -40 deg C, 2) ether, -78 to -20 deg C, then 2 h 6: 58 percent / MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 7: 90 percent / p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme