Tetrahedron: Asymmetry

A concise enantioselective synthesis of (+)-febrifugine

L Emmanuvel, DA Kamble, A Sudalai

Index: Emmanuvel, Lourdusamy; Kamble, Dayanand A.; Sudalai, Arumugam Tetrahedron Asymmetry, 2009 , vol. 20, # 1 p. 84 - 88

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Citation Number: 10

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.