A concise enantioselective synthesis of (+)-febrifugine |
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Authors: | Lourdusamy Emmanuvel Dayanand A. Kamble Arumugam Sudalai |
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Affiliation: | National Chemical Laboratory, Dr. Homi Bhabha Road, Chemical Engineering and Process Development Division, Pune 411008, Maharashtra, India |
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Abstract: | 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. |
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