1: zinc iodide / 0.17 h 2: 77 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature 3: NaNO2, 10percent acetic acid / other 1-substituted bicyclo<2.1.1>hexan-2-ones View Scheme

1: 98 percent / 1.) lithium diisopropylamide / tetrahydrofuran / 0.25 h / -78 °C 2: 58 percent / n-BuLi / diethyl ether; hexane / 0.5 h / -78 °C 3: toluene / 5 h / 0 °C 4: 1.26 g / K2CO3 / CH2Cl2 / 2 h / -78 °C 5: 1) m-chloroperbenzoic acid, 2.) diisopropylamine / 1.) -78 deg C, 30 min, 2.) -78 deg C -> RT View Scheme

1: zinc iodide / 0.17 h 2: 77 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature View Scheme