1: 1.) potassium hydroxide, 2.) 1 N hydrochloric acid / 1.) ethanol, water, RT, 20 h 2: 50 percent / silver nitrate, sodium hydroxide / ethanol; H2O / 24 h / Ambient temperature 3: oxalyl chloride / benzene / 3 h / Ambient temperature 4: pyridine / 3 h / 20 °C 5: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C, 15 min, 2.) from -30 deg C to 0 deg C 6: 99 percent / diisobutylaluminum hydride (Dibal-H) / CH2Cl2; hexane / 1 h / -10 °C 7: 89 percent / chromium trioxide, pyridine / CH2Cl2 / 1 h / 0 °C 8: 2.) water / 1.) ether, -78 deg C, 30 min, 2.) from -78 deg C to RT 9: 81 percent / chromium trioxide, pyridine / CH2Cl2 / 3 h / 0 °C 10: NaNH2 / benzene / 12 h / Heating View Scheme

1: 1.) potassium hydroxide, 2.) 1 N hydrochloric acid / 1.) ethanol, water, RT, 20 h 2: 50 percent / silver nitrate, sodium hydroxide / ethanol; H2O / 24 h / Ambient temperature 3: oxalyl chloride / benzene / 3 h / Ambient temperature 4: pyridine / 3 h / 20 °C 5: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C, 15 min, 2.) from -30 deg C to 0 deg C 6: 99 percent / diisobutylaluminum hydride (Dibal-H) / CH2Cl2; hexane / 1 h / -10 °C 7: 89 percent / chromium trioxide, pyridine / CH2Cl2 / 1 h / 0 °C 8: 2.) water / 1.) ether, -78 deg C, 30 min, 2.) from -78 deg C to RT 9: 81 percent / chromium trioxide, pyridine / CH2Cl2 / 3 h / 0 °C 10: LiNH2 / benzene / 90 h / Heating View Scheme