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You searched for +publisher:"Université Catholique de Louvain" +contributor:("Provins, Laurent"). Showing records 1 – 2 of 2 total matches.

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Université Catholique de Louvain

1. Philippart, Freddi. Vers la synthèse totale du Polycavernoside A.

Degree: 2012, Université Catholique de Louvain

Towards the total synthesis of Polycavernoside A. Polycavernoside A is a powerful marine toxin discovered 20 years ago in the red alga Polycavernosa tsudai (=Gracilaria edulis). For several years our laboratory is working on the total synthesis of this natural product. Its northern fragment having already been synthesised by Raphaël Dumeunier in our laboratory, we decided to prepare the southern part of the toxin by developing new methodologies in organic chemistry. Unprecedented preparations of tetrahydropyrans are therefore investigated, initially in a methodological view point and further in the total synthesis of the southern fragment of Polycavernoside A. The diastereoselective methodology developed for the preparation of those tetrahydropyrans is mainly based on two transformations, the ene reaction and the intermolecular Sakurai cyclisation (IMSC). By this way we hope to integrate the different substituents of the finale molecule and fix its stereochemistry. The main issue of this research is the better understanding of the reaction mechanisms and the transitions states of the investigated reactions, in order to develop a short and efficient pathway towards tetrahydropyrans. These cyclic compounds are quite common in natural products, like in the southern part of the Polycavernoside A. In the second part of our report, the synthesis of the southern and the northern part of the Polycavernoside A are illustrated and also some experiments of the coupling between the two parts are investigated.

Depuis plusieurs années, notre laboratoire s’intéresse à l’élaboration d’une méthode facile, concise et efficace pour la synthèse totale du Polycavernoside A. Le Polycavernoside A est une toxine marine glycosidique, issue de deux algues rouges Gracilaria edulis (= Polycavernosa tsudai) et Acanthophora specifera. Un chemin réactionnel original et efficace pour la synthèse du fragment nord de ce produit naturel a été élaboré par Raphaël Dumeunier durant sa thèse dans notre laboratoire. L’objectif de notre thèse est donc le développement d’une méthodologie diastéréosélective vers la préparation de tétrahydropyrannes, notamment le fragment sud du Polycavernoside A. Cette méthodologie est basée principalement sur deux transformations: une réaction ène et une condensation IMSC (réaction intermoléculaire de Sakurai), grâce auxquelles nous espérons pouvoir introduire les substituants présents dans la molécule finale et contrôler leur stéréochimie. L’enjeu principal de cette étude est une meilleure compréhension des mécanismes réactionnels, et donc des états de transition, de ces deux processus, afin de développer une voie rapide et efficace vers la synthèse des tétrahydropyrannes-cibles. Ces composés cycliques à 6 chaînons sont relativement courants dans de nombreux produits naturels de structures variées. Dans la seconde partie de notre travail, nous décrirons l’application de cette méthodologie à la synthèse diastéréocontrôlée du fragment sud du Polycavernoside, ainsi que la préparation du fragment nord de ce même produit…

Advisors/Committee Members: UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity, Markó, Istvan, Gohy, Jean-François, Riant, Olivier, Ollevier, Thierry, Provins, Laurent, Lanners, Steve.

Subjects/Keywords: Réaction ène; Condensation IMSC; Synthèse totale du fragment sud du Polycavernoside A

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Philippart, F. (2012). Vers la synthèse totale du Polycavernoside A. (Thesis). Université Catholique de Louvain. Retrieved from http://hdl.handle.net/2078.1/114623

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16th Edition):

Philippart, Freddi. “Vers la synthèse totale du Polycavernoside A.” 2012. Thesis, Université Catholique de Louvain. Accessed May 07, 2021. http://hdl.handle.net/2078.1/114623.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7th Edition):

Philippart, Freddi. “Vers la synthèse totale du Polycavernoside A.” 2012. Web. 07 May 2021.

Vancouver:

Philippart F. Vers la synthèse totale du Polycavernoside A. [Internet] [Thesis]. Université Catholique de Louvain; 2012. [cited 2021 May 07]. Available from: http://hdl.handle.net/2078.1/114623.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Philippart F. Vers la synthèse totale du Polycavernoside A. [Thesis]. Université Catholique de Louvain; 2012. Available from: http://hdl.handle.net/2078.1/114623

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation


Université Catholique de Louvain

2. Henroteaux, Géraldine. Towards novel analogues of Jerangolid D.

Degree: 2015, Université Catholique de Louvain

The continuous growth of fungal infections, coupled with the increased resistance of many microorganisms towards antifungal compounds, is an alarming health problem and the discovery of new antifungal agents has become a particularly important area of research. Jerangolid D is a potential antifungal agent of major interest. Recently, the first total synthesis of this natural product has been reported by our group. Its structure can be divided into three subunits: a substituted dihydropyran, an unsaturated lactone and a skipped 1,4-diene middle fragment. Our purpose is to operate a series of chemical modifications on these three subunits in order to create a set of new compounds, similar to Jerangolid D, but possessing hopefully enhanced stability, increased activity and lower toxicity. In this thesis, we shall initially describe our efforts towards the synthesis of the substituted dihydropyran. In order to do so, two methodologies have been developed, based upon previous work in our laboratory. The second one gave the best results and enabled access to the desired dihydropyran in 6 operations using an intramolecular silyl modified Sakurai cyclisation (ISMS) as the key step. The same pathway was used to construct new dihydropyrans by modifying the C-C triple bond. With the natural DHP in hand, different modifications were applied to the double bond in order to reach the right-hand fragment of jerangolid B, E and H in which the stereochemistry at C14 was still unknown. Subsequently, we will describe our efforts towards the preparation of the left-hand lactone of jerangolid D as well as a set of new analogues. Finally, we will present some preliminary investigations on the synthesis of new analogues of the central part of these natural products.

(SC - Sciences)  – UCL, 2015

Advisors/Committee Members: UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity, UCL - Faculté des Sciences, Marko, Istvan, Peeters, Daniel, Elias, Benjamin, Provins, Laurent, Vincent, Stéphane, Dobbs, Adrian.

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Henroteaux, G. (2015). Towards novel analogues of Jerangolid D. (Thesis). Université Catholique de Louvain. Retrieved from http://hdl.handle.net/2078.1/156663

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16th Edition):

Henroteaux, Géraldine. “Towards novel analogues of Jerangolid D.” 2015. Thesis, Université Catholique de Louvain. Accessed May 07, 2021. http://hdl.handle.net/2078.1/156663.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7th Edition):

Henroteaux, Géraldine. “Towards novel analogues of Jerangolid D.” 2015. Web. 07 May 2021.

Vancouver:

Henroteaux G. Towards novel analogues of Jerangolid D. [Internet] [Thesis]. Université Catholique de Louvain; 2015. [cited 2021 May 07]. Available from: http://hdl.handle.net/2078.1/156663.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Henroteaux G. Towards novel analogues of Jerangolid D. [Thesis]. Université Catholique de Louvain; 2015. Available from: http://hdl.handle.net/2078.1/156663

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

.