1: 81 percent / aq. AcOH / tetrahydrofuran / 45 °C 2: 75 percent / CrO3/pyridine / CH2Cl2 / 0 °C 3: LDA / tetrahydrofuran / -78 deg C, 8 h; -20 deg C, 1 h; room temp., 1 h 4: 60 percent / H2 / Lindlar catalyst / CH2Cl2 / 22 h / Ambient temperature 5: 73 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature View Scheme

1: 92 percent / PPh3, CBr4 / CH2Cl2 / -40 - 0 °C 2: 81 percent / aq. AcOH / tetrahydrofuran / 45 °C 3: 75 percent / CrO3/pyridine / CH2Cl2 / 0 °C 4: LDA / tetrahydrofuran / -78 deg C, 8 h; -20 deg C, 1 h; room temp., 1 h 5: 60 percent / H2 / Lindlar catalyst / CH2Cl2 / 22 h / Ambient temperature 6: 73 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature View Scheme

1: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2a.) THF, hexane, -78 deg C, 40 min, 2b.) -20 deg C, 30 min 2: 48 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h / 25 °C 3: 68 percent / K2CO3 / methanol; H2O / 12 h / Ambient temperature View Scheme

2: 99 percent / imidazole / dimethylformamide / 2 h / 23 °C 3: 82 percent / aq. LiOH / methanol / 0 °C 4: 88 percent / tetra-n-propylammonium perruthenate, N-methylmorpholine N-oxide, 4A-molecular sieves / CH2Cl2 / 23 °C 5: 84 percent / benzene / 15 h / 60 °C 6: 1) LiN(SiMe3)2 / 1) THF, -78 deg C, 1 h, 2) THF, a) -78 deg C, 1 h, b) -20 deg C, 1 h, c) 0 deg C, 1 h 7: 88 percent / H2, quinoline / BaSO4/Pd / ethyl acetate / 4 h / 23 °C 8: 82 percent / n-Bu4NF / tetrahydrofuran / 14 h / 23 °C View Scheme

1: 93 percent / Et2NH, Pd(PPh3)4, CuI / 15 h / Ambient temperature 2: 92 percent / PPh3, CBr4 / CH2Cl2 / -40 - 0 °C 3: 90 percent / 100 °C 4: LDA / tetrahydrofuran / -78 deg C, 8 h; -20 deg C, 1 h; room temp., 1 h 5: 60 percent / H2 / Lindlar catalyst / CH2Cl2 / 22 h / Ambient temperature 6: 73 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature View Scheme

1: 80 percent / KF.2H2O / dimethylformamide 2: 96 percent / imidazole / dimethylformamide 3: 93 percent / Et2NH, Pd(PPh3)4, CuI / 15 h / Ambient temperature 4: 92 percent / PPh3, CBr4 / CH2Cl2 / -40 - 0 °C 5: 90 percent / 100 °C 6: LDA / tetrahydrofuran / -78 deg C, 8 h; -20 deg C, 1 h; room temp., 1 h 7: 60 percent / H2 / Lindlar catalyst / CH2Cl2 / 22 h / Ambient temperature 8: 73 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, -78 deg C, 20 min 2: 27 percent / Et3N, DMAP / Ambient temperature 3: 97 percent / K2CO3 / methanol; H2O / 2 h / 25 °C 4: 99 percent / imidazole / dimethylformamide / 3 h / 35 °C 5: 1.) Cp2Zr(Cl)H, 2.) I2 / 1.) benzene, 40 deg C, 2.) hexane, 5 min 6: 95 percent / <(Ph3P)4Pd>, n-BuNH2, CuI / benzene / 0.5 h 7: 85 percent / AgNO3, KCN / aq. ethanol / 0.5 h / 30 °C 8: 1.) Cp2Zr(Cl)H, 2.) I2 / 1.) THF, 35 deg C, 15 min 9: 78 percent / n-butylamine, copper iodide / Pd<P(Ph3)>4 / benzene / 3 h / Ambient temperature 10: Bu4NF / tetrahydrofuran / 2 h / Ambient temperature 11: 85 percent 12: 65 percent / Zn, MeOH / H2O / 5 h / 30 °C 13: 95 percent / K2CO3 / methanol; H2O / Ambient temperature View Scheme

1: hydrogen / 10percent palladium-on-charcoal / ethyl acetate / 4 h / 23 °C 2: pyridine / 12 h / 23 °C 3: 1.) 2percent methanolic HCl, 2.) potassium carbonate / 1.) 23 deg C, 7 h, 2.) methanol, 23 deg C, 30 min 4: pyridine / 1 h / 23 °C 5: 1.) 70percent perchloric acid, dimethyl carbonate, 2.) lead tetracetate, sodium carbonate / 1.) water, 23 deg C, 4 h, 2.) methylene chloride, -40 deg C, 10 min 6: 32 percent / n-butyllithium, HMPA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C -> -20 deg C, 30 min, 3.) -20 deg C -> 0 deg C, 30 min 7: 1.) potassium carbonate, 2.) lithium hydroxide / 1.) methanol, 25 deg C, 6.5 h, 2.) methanol-water (2:1) 23 deg C, 1 h View Scheme

tetrabutyl ammonium fluoride in tetrahydrofuran T=0°C; 15 h;

1: 95 percent / <(Ph3P)4Pd>, n-BuNH2, CuI / benzene / 0.5 h 2: 85 percent / AgNO3, KCN / aq. ethanol / 0.5 h / 30 °C 3: 1.) Cp2Zr(Cl)H, 2.) I2 / 1.) THF, 35 deg C, 15 min 4: 78 percent / n-butylamine, copper iodide / Pd<P(Ph3)>4 / benzene / 3 h / Ambient temperature 5: Bu4NF / tetrahydrofuran / 2 h / Ambient temperature 6: 85 percent 7: 65 percent / Zn, MeOH / H2O / 5 h / 30 °C 8: 95 percent / K2CO3 / methanol; H2O / Ambient temperature View Scheme