1.1: 96 percent / dimethylsulfoxide / 3 h / 20 °C 2.1: zirconocene chloride hydride / benzene / 6 h / 20 °C 2.2: 74 percent / I2 / benzene 3.1: Pd(PPh3)4 / benzene / 0.25 h / 20 °C 3.2: 71 percent / benzene / 20 °C 4.1: 82 percent / PPTs / methanol / 24 h / 20 °C View Scheme

1: 85 percent / Mg / tetrahydrofuran / Heating 2: 86 percent / Me2S / copper(I) iodide / tetrahydrofuran / 1 h / -78 °C 3: 65 percent / 5N KOH / 3 h / Heating View Scheme

in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide 12 h;

in dimethyl sulfoxide T=20°C; Condensation; 3 h;

1: 1.) BuLi / 1.) THF 2: methanol 3: NaBH4 / H2O; CCl4 4: 2.) KOH / 1.) CH3OH 2.) 10N KOH 5: TsOH / tetrahydrofuran 6: 88 percent / ethanol 7: Li2CuCl4 / tetrahydrofuran / -25 - 0 °C 8: TsOH / methanol 9: pyridine View Scheme