Yield given. Multistep reaction;

1: 72 percent / p-toluenesulfonic acid, molecular sieves 4 A / toluene / Heating 2: 1) butyllithium, diisopropylamine / 1) hexane, THF,-70 deg C, 30 min, 2) THF, 15 min 3: 1) ozone, 2) pyridine / 1) CH2Cl2, -74 deg C, 2 h, 2) -74 deg C up to room temp. View Scheme

1: 1) thionyl chloride / 1a) room temp., 1 h, 1b) reflux, 30 min. 2: 32.5 g / 1.5 h / 150 °C / 15 Torr 3: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature 4: 72 percent / p-toluenesulfonic acid, molecular sieves 4 A / toluene / Heating 5: 1) butyllithium, diisopropylamine / 1) hexane, THF,-70 deg C, 30 min, 2) THF, 15 min 6: 1) ozone, 2) pyridine / 1) CH2Cl2, -74 deg C, 2 h, 2) -74 deg C up to room temp. View Scheme

1: 32.5 g / 1.5 h / 150 °C / 15 Torr 2: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature 3: 72 percent / p-toluenesulfonic acid, molecular sieves 4 A / toluene / Heating 4: 1) butyllithium, diisopropylamine / 1) hexane, THF,-70 deg C, 30 min, 2) THF, 15 min 5: 1) ozone, 2) pyridine / 1) CH2Cl2, -74 deg C, 2 h, 2) -74 deg C up to room temp. View Scheme

1: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature 2: 72 percent / p-toluenesulfonic acid, molecular sieves 4 A / toluene / Heating 3: 1) butyllithium, diisopropylamine / 1) hexane, THF,-70 deg C, 30 min, 2) THF, 15 min 4: 1) ozone, 2) pyridine / 1) CH2Cl2, -74 deg C, 2 h, 2) -74 deg C up to room temp. View Scheme

1.1: toluene-4-sulfonic acid / |Inert atmosphere 2.1: (phenylsulfonyl)methane / tetrahydrofuran / |Inert atmosphere 2.2: 105 - 110 °C / |Inert atmosphere View Scheme

pyridine; ozone 1) CH2Cl2, -74 deg C, 2 h, 2) -74 deg C up to room temp.; Yield given. Multistep reaction;