1: 85 percent / DIBAL / CH2Cl2 / -78 °C 2: 100 percent / 0 °C 3: 70 percent / Ph3P / CH2Cl2 / 0 °C 4: 80 percent / DIBAL / CH2Cl2 / -78 °C 5: 90 percent / Et3N, DMAP / CH2Cl2 6: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C to reflux View Scheme

1: 100 percent / 0 °C 2: 70 percent / Ph3P / CH2Cl2 / 0 °C 3: 80 percent / DIBAL / CH2Cl2 / -78 °C 4: 90 percent / Et3N, DMAP / CH2Cl2 5: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C to reflux View Scheme

1: 90 percent / Et3N, DMAP / CH2Cl2 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C to reflux View Scheme

1: 70 percent / Ph3P / CH2Cl2 / 0 °C 2: 80 percent / DIBAL / CH2Cl2 / -78 °C 3: 90 percent / Et3N, DMAP / CH2Cl2 4: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C to reflux View Scheme

1: 80 percent / DIBAL / CH2Cl2 / -78 °C 2: 90 percent / Et3N, DMAP / CH2Cl2 3: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C to reflux View Scheme

n-butyllithium 1.) THF, -78 deg C, 2.) -78 deg C to reflux; Yield given. Multistep reaction;