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Approches de synthèse du tricycle ABC du FR182877.

Abstract : This manuscript describes the work performed at the Ecole Polytechnique (November 2001 - September 2004) under the direction of Dr. Joëlle Prunet Synthesis in the Laboratory Organic headed by Professor Samir Zard. It details several approaches to synthesis of the tricycle ABC of FR182877, a new antimitotic agent found naturally in 1998. After presenting the FR182877 and different approaches to literature its total synthesis, the retrosynthesis proposed to construct the tricyclic ABC system using a strategy involving a Diels-Alder intermolecular reaction and ene-yne metathesis is detailed (Chapter I). The reaction of ene-yne metathesis will then the subject of a literature review (Chapter II) and its implementation in the context an approach to synthesis of ring A of FR182877 is described (Chapter III). Chapter Next (Chapter IV) for the second key step in the retrosynthetic scheme: the reaction Diels-Alder intermolecular and focuses on a methodological study carried out in the to understand the origin of an unexpected selectivity in the cycloaddition step. The Chapter V presents the results obtained in the context of a second retrosynthesis FR182877 based on a conjugate addition reaction of Michael. Finally, continuity this work, a quick and original functionalized tricyclic systems based on a series of tandem metathesis reactions has been developed and will be exhibited in the last chapter (Chapter VI). The experimental protocols and the description of synthesized products are presented in the experimental part, written in English.
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Submitted on : Thursday, July 29, 2010 - 10:00:25 AM
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Jacques-Alexis Funel. Approches de synthèse du tricycle ABC du FR182877.. Chimie. Ecole Polytechnique X, 2004. Français. ⟨pastel-00002300⟩

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