1: With ozone in methanol; dichloromethane T=-78°C; 2: With dimethylsulfide; toluene-4-sulfonic acid in methanol; dichloromethane T=-78 - 20°C; 3: With amberlyst-15 in acetone T=20°C;

1.1: O3 / methanol; CH2Cl2 / -78 °C 1.2: Me2S; p-CH3C6H4SO3H / methanol; CH2Cl2 / -78 - 20 °C 1.3: 98 percent / amberlyst-15 / acetone / 20 °C 2.1: 76 percent / H2 / Pd/C / methanol; tetrahydrofuran / 25 °C / 3040 Torr View Scheme