Etudes de nouvelles stratégies pour la synthèse modulaire de polyéthers naturels
(2010)
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- Authors
- Supervisors
- Markó, Istvan E.
- Abstract
- (en) Marine polycyclic ethers belong to one of the most outstanding and characteristic families of compounds produced by dinoflagellates.These powerful toxins are responsible of spectacular natural phenomenons known as the "red tides" or involved in food poisoning due to the consummation of toxic coral reef fishes. This work illustrates the development of a new methodology for the synthesis of these kind of compounds through an "ene-I.M.S.C." sequence. The key step of this strategy involves a double I.M.S.C. reaction between an ene adduct and tetramethoxypropane. The obtained bis-pyranic compound is engaged in a cyclization step, involving the reduction of a hemiketal moiety, to generate the central ring. These tricycles are easily obtained in good yields and with a diastereoselective control. However, the selectivity could be improved by using optically pure ene adducts. We explored as well various strategies to obtain those above with high enantiomeric excess.
- Affiliations
Citations
Delhaize, C. (2010). Etudes de nouvelles stratégies pour la synthèse modulaire de polyéthers naturels. https://hdl.handle.net/2078.5/148172