Vers la synthèse totale du Polycavernoside A
(2012)
Files
ThesePhilippartFreddi.pdf
Open Access - Adobe PDF
- 2.32 MB
Details
- Authors
- Supervisors
- Markó, Istvan
- Abstract
- (en) 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.
- Affiliations
Citations
Philippart, F. (2012). Vers la synthèse totale du Polycavernoside A. https://hdl.handle.net/2078.5/160402