EventsThe 12th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-12-01212
This submission belongs to the session a. General Organic Synthesis of the event The 12th International Electronic Conference on Synthetic Organic Chemistry
Published date
23 Nov, 2008
Citation
Eric Deniau, Marc Lamblin, Axel Couture, Pierre Grandclaudon, Asymmetric Synthesis of (+)-Coniine,(-)-Coniceine, (+)-b-Conhydrine,(+)-Sedamine and(+)-Allosedamine by a Strategic Combination of RCM with Nucleophilic 1,2-Addition on SAMP-Hydrazones, in Proceedings of The 12th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2008, MDPI: Basel, Switzerland, 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 1
Marc Lamblin 1
Axel Couture 1
Pierre Grandclaudon 1
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.
Keywords
n/a
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