1: H2 / Rh/Al2O3 2: 1.) LDA, 2.) I2 / 1.) THF, hexane, from -78 to 0 deg C, 2.5 h, 2.) THF, hexane, from -78 deg C to RT View Scheme

iodine; lithium diisopropyl amide 1.) THF, hexane, from -78 to 0 deg C, 2.5 h, 2.) THF, hexane, from -78 deg C to RT; Multistep reaction;

1: aq. KOH / methanol / Heating 2: 1.) HgO, 2.) Br2 / 1.) CH2Cl2, reflux, irradiation, 2.) CH2Cl2, reflux 3: 1.) tert-BuLi / 1.) THF, pentane, -78 deg C, 5 min, 2.) THF, pentane, from -78 deg C to RT View Scheme

1: LAH 2: activated dimethylsulfoxide 3: bis Wittig olefination View Scheme