1: 1. n-butyllithium / 1. DME, hexane, -78 deg C, 75 min 2. 10 deg C, 23 h 2: 92 percent / H2 / NaBH4, Ni(Ac)2*4H2O, ethylene diamine / ethanol / 2 h 3: 73 percent / NEt3 / diethyl ether / 0 °C 4: 86 percent / NaI, K2CO3 / acetone / 168 h / 35 °C 5: 76 percent / K2CO3 / acetonitrile / 72 h / 45 °C 6: 1. n-butyllithium / 1. -20 deg C, THF, hexane 2. a. -80 deg C, b. warm up to -10 deg C, 75 min c. 90 min, -10 deg C 7: 68 percent / aq. oxalic acid / tetrahydrofuran / 1 h / Ambient temperature 8: 86 percent / K2CO3 / 1 h / 23 °C 9: 13.5 mg / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C 10: aq. NaOH / methanol / 5 h / Ambient temperature View Scheme

boron trifluoride diethyl etherate in dichloromethane T=-15°C; 10 h;

in tetrahydrofuran; N,N-dimethyl-formamide; paraffin; xylene 20 h; 1. -80 deg C to -75 deg C, 90 min, 2. to room temperature, 2 h 3. room temperature;

1: 20percent KOH in ethanol / various solvent(s) / 0.25 h / Heating 2: pyridine / CH2Cl2 / 0 °C 3: 90 percent / BF3*Et2O / CH2Cl2 / 10 h / -15 °C View Scheme

1: 80 percent / BF3*Et2O / CH2Cl2 / 1. -10 deg C to 0 deg C, 2 h 2. 0 deg C, 7 h 2: 81 percent / tetrahydrofuran; dimethylformamide; paraffin; xylene / 20 h / 1. -80 deg C to -75 deg C, 90 min, 2. to room temperature, 2 h 3. room temperature View Scheme

iodine; silver trifluoroacetate