1: oxalic acid, 2,5-di-tert-butylhydroquinone / acetone; H2O / 2 h / Heating 2: 1) n-BuLi / 1) THF, hexane, -60 deg C, 1h, 2) 0 deg C, 1h 3: 44 percent / t-BuOOH, Ti(O-i-Pr)4, L-(+)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / 4 h / -21 °C 4: 86 percent / t-BuOOH, d-(-)-DIPT, Ti(O-i-Pr)4, molecular sieves 4 Angstroem / CH2Cl2 / 4 h / -21 °C 5: imidazole / dimethylformamide / Ambient temperature 6: 1) Bu3SnLi, 2) I2 / 1) THF, 0 deg C, 3h, 2) Et2O, 0 deg C, 0.5h 7: 1) disiamylborane, 2) LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h, 2) 40 deg C, 18h 8: 85 percent / n-Bu4NF / tetrahydrofuran / 17 h / Ambient temperature View Scheme

oxalic acid in water; acetone T=60°C; 1 h;

1: 93 percent / oxalic acid / acetone; H2O / 1 h / 60 °C 2: 62 percent / n-BuLi / tetrahydrofuran / 1 h / -78 °C View Scheme

1: oxalic acid, 2,5-di-tert-butylhydroquinone / acetone; H2O / 2 h / Heating 2: 1) n-BuLi / 1) THF, hexane, -60 deg C, 1h, 2) 0 deg C, 1h View Scheme

hydrogen; Pd-BaSO4 in methanol 30 h;

1: 63 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / 2 h / Heating 2: 83 percent / quinoline; H2 / Lindlar catalyst / ethanol / 2 h View Scheme

1: 63 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / 2 h / Heating 2: 83 percent / quinoline; H2 / Lindlar catalyst / ethanol / 2 h View Scheme

1: 93 percent / oxalic acid / acetone; H2O / 1 h / 60 °C 2: 62 percent / n-BuLi / tetrahydrofuran / 1 h / -78 °C 3: 69 percent / 7 h / Heating 4: 47 percent Chromat. / Al2O3 / benzene / 1 h / Heating View Scheme

1: 93 percent / oxalic acid / acetone; H2O / 1 h / 60 °C 2: 62 percent / n-BuLi / tetrahydrofuran / 1 h / -78 °C 3: 69 percent / 7 h / Heating 4: 47 percent Chromat. / Al2O3 / benzene / 1 h / Heating 5: 58 percent / LiAlH4 / diethyl ether / 1.5 h / -40 °C View Scheme

1: 93 percent / oxalic acid / acetone; H2O / 1 h / 60 °C 2: 62 percent / n-BuLi / tetrahydrofuran / 1 h / -78 °C 3: 69 percent / 7 h / Heating View Scheme