diisobutylaluminium hydride in toluene T=-78°C; Reduction;

sodium periodate; sodium hydrogencarbonate in ethanol; dichloromethane; water

1: LAH / diethyl ether 2: O3, DMS / CH2Cl2 View Scheme

1: BuLi / CH2Cl2 2: LAH / diethyl ether 3: O3, DMS / CH2Cl2 View Scheme

dimethylsulfide; ozone 1.) CH2Cl2, -78 deg C, 2.) r.t., 4 h; Yield given. Multistep reaction;

1: formaldehyd; hydroxyacetaldehyde T=65°C; 1 h; borate buffer; 2: acetone With sulfuric acid 1.5 h;

sulfuric acid

1: 1.) t-BuOK / 1.) THF, r.t., 1 h, 2.) -78 to r.t., 3 h 2: PCC, NaOAc, MS 4A / CH2Cl2 / 5 h / Ambient temperature 3: aq. NaH2PO4, NaClO2, 2-methylbut-2-ene / 2-methyl-propan-2-ol / 1.5 h / 25 - 30 °C 4: 94 percent / diethyl ether / 0.5 h / 0 °C 5: 2.7 percent / MCPBA / CH2Cl2 / 12 h / Ambient temperature View Scheme