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: 98 percent / 15percent hydrogen fluoride/pyridine mixture / acetonitrile / 1.) 0 deg C; 2.) 24 deg C, 30 min; 3.) 24 deg C, 3 h 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: 98 percent / 15percent hydrogen fluoride/pyridine mixture / acetonitrile / 1.) 0 deg C; 2.) 24 deg C, 30 min; 3.) 24 deg C, 3 h View Scheme

1: 51 percent / Mo[N(t-Bu)(3,5-diMePh)]3/CH2Cl2 / toluene; CH2Cl2 / 9 h / 80 °C 2: 87 percent / H2; quinoline / Lindlar catalyst / hexane / 760.05 Torr 3: 88 percent / aq. HF / tetrahydrofuran / 1 h View Scheme

1: 85 percent / p-toluenesulfonic acid hydrate / 36 h / Heating 2: hydrogen / Lindlar catalyst / hexane; ethyl acetate / 0 °C 3: 96 percent / carbon tetrabromide, triphenylphosphine / CH2Cl2 / 0.67 h 4: 99.9 percent / NaI / acetone / 0.08 h / with longer reaction time the cis-isomer began to isomerized to trans-isomer 5: 1.) n-BuLi; 2.) CuI-Bu3P, and Bu3P / 1.) THF, -78 deg C, 20 min, 30 min; 2.) THF, ether, -78 deg C 10 min, - 30 deg C 1 h; 3.) THF, ether, HMPA, -30 deg C, 3 h 6: 78 percent / pyridine, 50percent aq. HF / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 7: aluminum amalgam / tetrahydrofuran; H2O / addition in equal portion after 10 h, 17 h and 23h; rt 15 h 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: 98 percent / 15percent hydrogen fluoride/pyridine mixture / acetonitrile / 1.) 0 deg C; 2.) 24 deg C, 30 min; 3.) 24 deg C, 3 h View Scheme

formaldehyd; boron trifluoride diethyl etherate in water; acetone 120 h; Ambient temperature;

1: 1.) n-BuLi; 2.) CuI-Bu3P, and Bu3P / 1.) THF, -78 deg C, 20 min, 30 min; 2.) THF, ether, -78 deg C 10 min, - 30 deg C 1 h; 3.) THF, ether, HMPA, -30 deg C, 3 h 2: 78 percent / pyridine, 50percent aq. HF / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 3: aluminum amalgam / tetrahydrofuran; H2O / addition in equal portion after 10 h, 17 h and 23h; rt 15 h View Scheme

1: 1.) n-BuLi; 2.) CuI-Bu3P, and Bu3P / 1.) THF, -78 deg C, 20 min, 30 min; 2.) THF, ether, -78 deg C 10 min, - 30 deg C 1 h; 3.) THF, ether, HMPA, -30 deg C, 3 h 2: 78 percent / pyridine, 50percent aq. HF / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 3: aluminum amalgam / tetrahydrofuran; H2O / addition in equal portion after 10 h, 17 h and 23h; rt 15 h View Scheme

1: 78 percent / pyridine, 50percent aq. HF / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 2: aluminum amalgam / tetrahydrofuran; H2O / addition in equal portion after 10 h, 17 h and 23h; rt 15 h View Scheme

1: 87 percent / H2 / Lindlar catalyst / CH2Cl2 / 760.05 Torr 2: 88 percent / aq. HF / tetrahydrofuran View Scheme