1: 1.) BuLi, CuC5H11 2: 95 percent / sulphuric acid, H2O 3: 98 percent / peracetic acid / -78 °C View Scheme

2: 1.) CuCN 3: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 4: CrO3, H+ 5: aq. HF / acetonitrile View Scheme

1: 1.) BuLi, CuC5H11 2: 95 percent / sulphuric acid, H2O 3: 98 percent / peracetic acid / -78 °C View Scheme

1: 1.) BuLi, CuC5H11 2: 95 percent / sulphuric acid, H2O 3: acetonitrile; H2O / Irradiation 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

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

Yield given. Multistep reaction. Yields of byproduct given;

2: 92 percent / hydrogenfluoride-pyridine / acetonitrile / 3 h / Ambient temperature 3: 89 percent / 18 h / Ambient temperature; hydrolysis porcine liver esterase View Scheme