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 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

sodium acetate; copper dichloride in water; acetone

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 View Scheme