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Asymmetric Synthesis of (+)-Coniine,(-)-Coniceine, (+)-b-Conhydrine,(+)-Sedamine and(+)-Allosedamine by a Strategic Combination of RCM with Nucleophilic 1,2-Addition on SAMP-Hydrazones
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1  UMR CNRS 8009 "Chimie Organique et Macromoléculaire", Université des Sciences et Technologies de Lille 1, Laboratoire de Chimie Organique Physique, Bâtiment C3(2), F-59655 Villeneuve d'Ascq Cedex, France

Abstract: A tactically new approach to the asymmetric synthesis of the piperidine alkaloids (+)-coniine, (-)-coniceine, (+)-b -conhydrine, (+)-sedamine and (+)-allosedamine has been developed. The key step is the elaboration of the piperidine template equipped with suitably functionalized appendages at the stereodefined C-2 position. Subsequent manipulation of the appropriate functionalities gave rise to the targeted compounds in high yields and high level of enantioselectivity.
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