1: LiOH 2: NaI / acetone 4: 81 percent / KN(SiMe3)2 / tetrahydrofuran / 0 °C 5: 98 percent / pyridine, (HF)x / tetrahydrofuran 6: 68 percent / DEAD, PH3P / benzene 7: 68 percent / Ce(NH4)2(NO3)6 / H2O; acetonitrile 8: HOAc / tetrahydrofuran; H2O / 60 °C View Scheme

1: 95 percent / 1.) nBuLi 2: -78 °C View Scheme

T=-78°C;

copper(l) iodide 1.) THF, ether, -10 deg C, 2.) THF, ether, -78 deg C, 1 h; Yield given. Multistep reaction;

sodium hydride in tetrahydrofuran; dimethyl sulfoxide 24 h; Ambient temperature; Yield given. Yields of byproduct given;

(i) NaH, 1,2-dimethoxy-ethane, (ii) /BRN= 1098490/; Multistep reaction;