1: dimethylformamide / Heating 2: camphorsulfonic acid / 9 h / Heating 3: 97 percent / H2 / Pd/C / ethanol / Ambient temperature 4: 84 percent / pyridine / 1 h / Ambient temperature 5: 82 percent / PPTS / benzene / 2 h / Heating View Scheme

1: O3 / methanol; CH2Cl2 / 2 h / -78 °C 2: 2.) camphorsulfonic acid / 1.) MeOH, CH2Cl2, room temp., 30 min; 2.) MeOH, CH2Cl2, room temp., 75 min 3: 97 percent / H2 / Pd/C / ethanol / Ambient temperature 4: 84 percent / pyridine / 1 h / Ambient temperature 5: 82 percent / PPTS / benzene / 2 h / Heating View Scheme

1: camphorsulfonic acid / 9 h / Heating 2: 97 percent / H2 / Pd/C / ethanol / Ambient temperature 3: 84 percent / pyridine / 1 h / Ambient temperature 4: 82 percent / PPTS / benzene / 2 h / Heating View Scheme

1: NaOAc, CuCl2 / H2O; acetone 2: O3 / methanol; CH2Cl2 / 2 h / -78 °C 3: 2.) camphorsulfonic acid / 1.) MeOH, CH2Cl2, room temp., 30 min; 2.) MeOH, CH2Cl2, room temp., 75 min 4: 97 percent / H2 / Pd/C / ethanol / Ambient temperature 5: 84 percent / pyridine / 1 h / Ambient temperature 6: 82 percent / PPTS / benzene / 2 h / Heating View Scheme

1: 97 percent / H2 / Pd/C / ethanol / Ambient temperature 2: 84 percent / pyridine / 1 h / Ambient temperature 3: 82 percent / PPTS / benzene / 2 h / Heating View Scheme

1: 84 percent / pyridine / 1 h / Ambient temperature 2: 82 percent / PPTS / benzene / 2 h / Heating View Scheme

sodium hydroxide in methanol 72 h; other reag.; other solvent; Product distribution;