Approches originales vers la synthèse totale de la Teuvincentine C
(2009)
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- Authors
- Supervisors
- Markó, Istvan
- Abstract
- (en) Teuvincentin C is a neo-clerodane diterpenoid isolated from Teucrium vincentinum, a shrub growing in Portugal. This compound exhibits a powerful antifeedant activity against insects. The desire to reproduce the tricky architecture of Teuvincentin C was at the heart of this work. To achieve this goal, we developed new strategies for the synthesis of the core nucleus of Teuvincentin C and analogous molecules. The first part of this work was focused on the asymmetric generation of three synthons resulting from the retrosynthetic pathway. Then, three different approaches were tested to construct the tricyclic core of Teuvincentin C. One of them led to the diastereoselective formation of the desired tricycle. This methodology is based upon the addition of a silyl ketene acetal derived from g-butyrolactone on a Michaël acceptor. Then, the use of p-allylpalladium complexes enabled us to reach the desired tricyclic nucleus.
- Affiliations
Citations
Lebrun, B. (2009). Approches originales vers la synthèse totale de la Teuvincentine C. https://hdl.handle.net/2078.5/128865