1: 1) ozone-oxygen mixture, 2) H2 / 2) Pd-CaCO3-PbO / 1) methanol, 0 deg C, 2) methanol, RT, 25 h 2: 85 percent / p-TsOH / methanol; H2O / 20 h / Ambient temperature 3: 91 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 4: 46 percent / piperidine, pyridine / 1) 22 deg C, 17 h, 2) 30 deg C, 6 h, then 120 deg C, 1.5 h View Scheme

1: 1) ozone-oxygen mixture, 2) H2 / 2) Pd-CaCO3-PbO / 1) methanol, 0 deg C, 2) methanol, RT, 25 h 2: 85 percent / p-TsOH / methanol; H2O / 20 h / Ambient temperature 3: 91 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature View Scheme