Asymmetric Synthesis of (+)-Coniine,(-)-Coniceine, (+)-b-Conhydrine,(+)-Sedamine and(+)-Allosedamine by a Strategic Combination of RCM with Nucleophilic 1,2-Addition on SAMP-Hydrazones

Eric Deniau; Marc Lamblin; Axel Couture; Pierre Grandclaudon

doi:10.3390/ecsoc-12-01212

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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

Eric Deniau

Marc Lamblin

Axel Couture

^*,

Pierre Grandclaudon

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

Published: 23 November 2008 by MDPI in The 12th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-12-01212

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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Eric Deniau

Marc Lamblin

Axel Couture

Pierre Grandclaudon