in tetrahydrofuran; water; acetic acid T=55°C; 1.5 h;

1: 1.) t-C4H9Li; copper(I) iodide, tributylphosphine; 3.) triphenyltin chloride / 1.) ether-pentane, -95 deg C, -78 deg C 3h; THF -78 deg C 15 min; 2.) ether, pentane, THF, -78 deg C 3.5 h, HPMA, -78 deg C 30 min; 3.) ether, pentane, THF, HMPA, -30 deg C, 39 h 2: 87 percent / hydrogen, synthetic quinoline / palladium on barium sulfate / benzene; cyclohexane / 1.) 25 deg C, 3 h; 2.) 40 deg C, 4.5 h 3: 1.) L-Selectride; 2.) 3percent H2O2 / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C 4: 85 percent / acetic acid / tetrahydrofuran; H2O / 1.5 h / 55 °C View Scheme

1: 1.) t-C4H9Li; copper(I) iodide, tributylphosphine; 3.) triphenyltin chloride / 1.) ether-pentane, -95 deg C, -78 deg C 3h; THF -78 deg C 15 min; 2.) ether, pentane, THF, -78 deg C 3.5 h, HPMA, -78 deg C 30 min; 3.) ether, pentane, THF, HMPA, -30 deg C, 39 h 2: 87 percent / hydrogen, synthetic quinoline / palladium on barium sulfate / benzene; cyclohexane / 1.) 25 deg C, 3 h; 2.) 40 deg C, 4.5 h 3: 1.) L-Selectride; 2.) 3percent H2O2 / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C 4: 85 percent / acetic acid / tetrahydrofuran; H2O / 1.5 h / 55 °C View Scheme

1: 87 percent / hydrogen, synthetic quinoline / palladium on barium sulfate / benzene; cyclohexane / 1.) 25 deg C, 3 h; 2.) 40 deg C, 4.5 h 2: 1.) L-Selectride; 2.) 3percent H2O2 / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C 3: 85 percent / acetic acid / tetrahydrofuran; H2O / 1.5 h / 55 °C View Scheme

tetrakis(triphenylphosphine) palladium(0) in dichloromethane T=19°C; 3 h;

1: 81 percent / hydrogen / Lindlar catalyst / benzene; cyclohexane / 12 h / 23 °C 2: 85 percent / acetic acid / tetrahydrofuran; H2O / 1.5 h / 55 °C View Scheme

aluminum(i-butyl)2(2,6-di-tert-butyl-4-methylphenoxy) in toluene T=-78 - -20°C; 3.5 h;

1: 1.) t-C4H9Li; copper(I) iodide, tributylphosphine; 3.) triphenyltin chloride / 1.) ether-pentane, -95 deg C, -78 deg C 3h; THF -78 deg C 15 min; 2.) ether, pentane, THF, -78 deg C 3.5 h, HPMA, -78 deg C 30 min; 3.) ether, pentane, THF, HMPA, -30 deg C, 39 h 2: 87 percent / hydrogen, synthetic quinoline / palladium on barium sulfate / benzene; cyclohexane / 1.) 25 deg C, 3 h; 2.) 40 deg C, 4.5 h 3: 1.) L-Selectride; 2.) 3percent H2O2 / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C 4: 85 percent / acetic acid / tetrahydrofuran; H2O / 1.5 h / 55 °C View Scheme

1: 1.) L-Selectride; 2.) 3percent H2O2 / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C 2: 85 percent / acetic acid / tetrahydrofuran; H2O / 1.5 h / 55 °C View Scheme

1: KOH / methanol; H2O / 12 h / Ambient temperature 2: 12 percent / 1.) BuLi, 3.) 50percent aq. AcOH / 1.) THF-Et2O, -78 deg C -> -20 deg C, 30 min, then -> -78 deg C, 2.) -78 deg C -> RT, 3.) 50 deg C, 1 h View Scheme