1: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C, 15 min, 2.) from -30 deg C to 0 deg C 2: 99 percent / diisobutylaluminum hydride (Dibal-H) / CH2Cl2; hexane / 1 h / -10 °C 3: 89 percent / chromium trioxide, pyridine / CH2Cl2 / 1 h / 0 °C 4: 2.) water / 1.) ether, -78 deg C, 30 min, 2.) from -78 deg C to RT 5: 81 percent / chromium trioxide, pyridine / CH2Cl2 / 3 h / 0 °C 6: NaNH2 / benzene / 12 h / Heating View Scheme

1: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C, 15 min, 2.) from -30 deg C to 0 deg C 2: 99 percent / diisobutylaluminum hydride (Dibal-H) / CH2Cl2; hexane / 1 h / -10 °C 3: 89 percent / chromium trioxide, pyridine / CH2Cl2 / 1 h / 0 °C 4: 2.) water / 1.) ether, -78 deg C, 30 min, 2.) from -78 deg C to RT 5: 81 percent / chromium trioxide, pyridine / CH2Cl2 / 3 h / 0 °C 6: LiNH2 / benzene / 90 h / Heating View Scheme