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Theses

Synthèse de composés polyspiranniques par oxydation phénolique -
Synthèse totale des aculéatines et d'analogues antipaludiques

Abstract : The aculeatins are natural and biologically active products isolated from Amomum aculeatum, a plant used in folk medicine of Papua New Guinea to treat fever and malaria. The synthetical approach developed for the total enantioselective synthesis of aculeatins exploits a phenolic oxidation linked to a spiroannulation as key reactions. While studying diastereoselective aldol reaction for the synthesis of aculeatins, the field of application of 1,3-anti induction (PMB) was enlarged to sterically non hindered substrates. In addition, we developed a 1,3-syn induction (Tr), reaction rarely described in the literature.
Once the synthesis achieved, two topics were developed. The first research thematic aimed at the study of the phenolic oxidation, and particularly, the study of the trapping of the phenoxonium cation by different sp2 heteroatoms: the oxygen atom of a ketone for the aculeatins, the oxygen atom of a lactam for the attempted synthesis of spiroleucettadine and the nitrogen atom of an oxazoline for a synthetical approach to the synthesis of TAN analogues.
On the biological aspect, the synthesis of aculeatins analogues allowed the evaluation of important parameters related with three biological activities (antimalarial, antitoxoplasmic, herbicide) having in common the plasts. The study of structure-activity relationships pointed out some structural characteristics for the optimization of biological properties. At the same time, in vivo studies of two biologically active molecules (IC50 = 80 and 90 nM) are ongoing.
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https://tel.archives-ouvertes.fr/tel-00188364
Contributor : Marine Peuchmaur <>
Submitted on : Friday, November 16, 2007 - 3:37:11 PM
Last modification on : Friday, November 6, 2020 - 3:43:49 AM
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Marine Peuchmaur. Synthèse de composés polyspiranniques par oxydation phénolique -
Synthèse totale des aculéatines et d'analogues antipaludiques. Autre. Université Joseph-Fourier - Grenoble I, 2007. Français. ⟨tel-00188364⟩

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