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Theses

Développement de nouvelles stratégies de synthèses d'alcaloïdes basées sur la métathèse d'oléfines hétérosubstituées : Synthèse de la (+)-castanospermine et de la 1-(+)-désoxynojirimycine.

Abstract : The work reported in this manuscript concerns the development of a new strategy for the synthesis of polyhydroxylated alkaloids based on a ring closing metathesis and enol ether hydroboration-oxidation sequence to access efficiently and selectively trans-trans triols in substituted piperidine. After the optimization of this sequence, the methodology was applied to the total synthesis of two natural products: (+)-castanospermine and (+)-1-deoxynojirimycin. A modification of this strategy was then explored for the synthesis of polyhydroxylated pyrrolidines based on a reaction of an enamide hydroboration-oxidation. The different approaches examined for obtaining the precursor cyclic enamide (for example ring closing metathesis of an enamide or an ynamide; a sequence of cross metathesis, bromation, and coupling), however, have not to date yielded the desired intermediate. Finally, an application of the ring closing metathesis and enol ether hydroboration-oxidation sequences has provided an advanced precursor for the synthesis of D-AB1.
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https://tel.archives-ouvertes.fr/tel-00560812
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Submitted on : Sunday, January 30, 2011 - 2:33:25 PM
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  • HAL Id : tel-00560812, version 1

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Grégory Danoun. Développement de nouvelles stratégies de synthèses d'alcaloïdes basées sur la métathèse d'oléfines hétérosubstituées : Synthèse de la (+)-castanospermine et de la 1-(+)-désoxynojirimycine.. Chimie. Université Joseph-Fourier - Grenoble I, 2010. Français. ⟨tel-00560812⟩

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