lithium hydroxide in water; isopropyl alcohol T=23°C; 1 h;

tetrabutyl ammonium fluoride in tetrahydrofuran T=23°C; 14 h;

1: 1) n-BuLi, 2) CuCl / 1) THF, hexane, -78 deg C, 20 min, 2) THF, a) -78 deg C, 45 min, b) to 5 deg C 2: S-Alpine-borane / tetrahydrofuran / 15 h / 23 °C 3: 99 percent / imidazole / dimethylformamide / 2.5 h / 23 °C 4: 82 percent / Br2, 1,2-bis(diphenylphosphino)ethane / CH2Cl2 / 0.08 h / 0 °C 5: 1) NaN(SiMe3)2 / 1) THF, -10 deg C, 15 min, 2) THF, -10 deg C, 1 h 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: 96 percent / imidazole / dimethylformamide 2: 93 percent / Et2NH, Pd(PPh3)4, CuI / 15 h / Ambient temperature 3: 92 percent / PPh3, CBr4 / CH2Cl2 / -40 - 0 °C 4: 90 percent / 100 °C 5: LDA / tetrahydrofuran / -78 deg C, 8 h; -20 deg C, 1 h; room temp., 1 h 6: 60 percent / H2 / Lindlar catalyst / CH2Cl2 / 22 h / Ambient temperature 7: 73 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature View Scheme

tetrabutyl ammonium fluoride in tetrahydrofuran 17 h; Ambient temperature;

1: 84 percent / benzene / 15 h / 60 °C 2: 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 3: 88 percent / H2, quinoline / BaSO4/Pd / ethyl acetate / 4 h / 23 °C 4: 82 percent / n-Bu4NF / tetrahydrofuran / 14 h / 23 °C View Scheme

1: 88 percent / tetra-n-propylammonium perruthenate, N-methylmorpholine N-oxide, 4A-molecular sieves / CH2Cl2 / 23 °C 2: 84 percent / benzene / 15 h / 60 °C 3: 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 4: 88 percent / H2, quinoline / BaSO4/Pd / ethyl acetate / 4 h / 23 °C 5: 82 percent / n-Bu4NF / tetrahydrofuran / 14 h / 23 °C View Scheme

1: 88 percent / H2, quinoline / BaSO4/Pd / ethyl acetate / 4 h / 23 °C 2: 82 percent / n-Bu4NF / tetrahydrofuran / 14 h / 23 °C View Scheme

1.1: LDA / tetrahydrofuran; cyclohexane / 1 h / -78 - 20 °C 1.2: 49 percent / I2 / CH2Cl2 / 0.5 h / 20 °C 2.1: 89 percent / H2; Lindlar catalyst / hexane 3.1: 63 percent / TBAF / tetrahydrofuran / 15 h / 0 °C View Scheme

1: 85 percent / (-)-9-pinanyl-BBN / tetrahydrofuran / 25 °C 2: 80 percent / KF.2H2O / dimethylformamide 3: 96 percent / imidazole / dimethylformamide 4: 93 percent / Et2NH, Pd(PPh3)4, CuI / 15 h / Ambient temperature 5: 92 percent / PPh3, CBr4 / CH2Cl2 / -40 - 0 °C 6: 90 percent / 100 °C 7: LDA / tetrahydrofuran / -78 deg C, 8 h; -20 deg C, 1 h; room temp., 1 h 8: 60 percent / H2 / Lindlar catalyst / CH2Cl2 / 22 h / Ambient temperature 9: 73 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature View Scheme