A short enantioselective synthesis of (+)-febrifugine, a potent antimalarial alkaloid, has been described based on the regioselective asymmetric dihydroxylation of a 1, 4-dienic ester as the key step. The strategy also involves chemoselective [3, 3]-sigmatropic rearrangement of 1, 5-hexadiene-3-ol and intramolecular lactamization of azidolactone for the construction of piperidine core.