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Approche Générale et Efficace des Terpénoïdes Possédant le Squelette Bicyclo[5.3.0]décane : Synthèse de Sesquiterpènes (Aromadendranes, Guaianes et Tri-nor-guaianes) et Approche des Diterpènes.

Abstract : The [2+2] cycloaddition of dichloroketene and monosubstituted cycloheptatrienes, followed by ring expansion with diazomethane and dehydrohalogenation, affords alpha-chlorotrienones in a regio- and stereoselective manner. These compounds are attractive synthons for the efficient total synthesis of natural products containing the bicyclo[5.3.0]decane skeleton. Regio- and diastereoselective cyclopropanation reaction of sulfure ylide with alpha-chlorotrienones gave a general approach to aromadendrane family. The total synthesis of (±)-cyclocolorenone has been achieved in a few steps. A selective hydrogenation was used for the efficient total synthesis of (±)-guaia-4,6-diene-3-one and for the formal synthesis of the (±)-clavukerin A. An efficient approach to diterpenes tricyclic skeleton, including daphnanes and tiglianes, has been achieved via a chimio-, regio-and stereoselective Diels-Alder reaction in only 3 steps from the cycloheptatriene.
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https://tel.archives-ouvertes.fr/tel-00331873
Contributor : Mihaela Calancea <>
Submitted on : Sunday, October 19, 2008 - 10:33:16 AM
Last modification on : Friday, November 6, 2020 - 4:04:18 AM
Long-term archiving on: : Monday, June 7, 2010 - 8:46:16 PM

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Mihaela Calancea. Approche Générale et Efficace des Terpénoïdes Possédant le Squelette Bicyclo[5.3.0]décane : Synthèse de Sesquiterpènes (Aromadendranes, Guaianes et Tri-nor-guaianes) et Approche des Diterpènes.. Chimie. Université Joseph-Fourier - Grenoble I, 2008. Français. ⟨tel-00331873⟩

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