1: CHCl3 / 3 h / 23 °C 2: sodium methoxide / tetrahydrofuran / 4 h / 23 °C 3: 82 percent / CuI / tetrahydrofuran / 3 h / -40 to 0 deg C 4: triphenylphosphine, diethyl azodicarboxylate, diphenylphosphoryl azide / toluene / 12 h / 0 to 23 deg C 5: 40 percent aq. acetic acid / 3 h / 90 °C 6: hydrogen / 10 percent Pd/charcoal / ethyl acetate; methanol / atmospheric pressure 7: 82 percent / N-ethyl-N'-(dimethylaminopropyl)carbodiimide hydrochloride, triethylamine, 1-hydroxybenzotriazole hydrate / dimethylformamide / 12 h View Scheme

1: aq. NaIO4; NaHCO3 / 1 h / 20 °C 2: 6.6 g / aq. K2CO3 / 6 h / 20 °C 3: H2 / Pd/C / ethanol 4: 100 percent / LiAlH4 / diethyl ether / 0 - 20 °C View Scheme

Multistep reaction;