1: 3-allylcyclohexan-1-one With ozone in dichloromethane T=-78°C; 2: With dimethylsulfide T=20°C; 12 h; 3: methyl (triphenylphosphoranylidene)acetate in dichloromethane T=20°C; Wittig type reaction;

1.1: O3 / CH2Cl2 / -78 °C 1.2: Me2S / 12 h / 20 °C 2.1: 85 percent / CH2Cl2 / 12 h / 20 °C View Scheme

1: HBr / hexane / Irradiation 2: NaI / acetone / 12 h / Heating 3: 1) t-BuLi, 2) H3O+ / 1) THF, -78 deg C View Scheme