pyridine T=4°C;

1: DABCO / tetrahydrofuran / 23 h / 18 °C 2: NEt3; DMAP / CH2Cl2 View Scheme

1: DIBAL / toluene / 7 h / -78 °C 2: oxalic acid / CH2Cl2; H2O / 3.5 h / Ambient temperature 3: 93 percent / pyridine / 4 °C View Scheme

1: 1.) n-BuLi, 2.) / 1.) THF, -78 deg C, 2.) -78 deg C 2: DIBAL / toluene / 7 h / -78 °C 3: oxalic acid / CH2Cl2; H2O / 3.5 h / Ambient temperature 4: 93 percent / pyridine / 4 °C View Scheme

1: 85 percent / TsOH*H2O / benzene / 43 h / Heating; azeotropic removal of water 2: 1.) n-BuLi, 2.) / 1.) THF, -78 deg C, 2.) -78 deg C 3: DIBAL / toluene / 7 h / -78 °C 4: oxalic acid / CH2Cl2; H2O / 3.5 h / Ambient temperature 5: 93 percent / pyridine / 4 °C View Scheme

1: 82 percent / fumaric acid / benzene / 68 h / Heating; azeotropic removal of water 2: DIBAL / toluene / 7 h / -78 °C 3: oxalic acid / CH2Cl2; H2O / 3.5 h / Ambient temperature 4: 93 percent / pyridine / 4 °C View Scheme

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