Etude de nouvelles réactions péricycliques en cascade : application à la synthèse d'exo-méthylène-butyrolactones
(2006)
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- Authors
- Supervisors
- Marko, Istvan E.
- Abstract
- (en) Our laboratory is interested in the development of a simple, concise and broad method for the synthesis of a-methylene-g-butyrolactones. These lactones are ubiquitous subunits in a wide variety of biologically active natural products (anticancer, antiallergenic and antibiotic). Our Ph. D. work began with the development of a novel procedure for the efficient and flexible preparation of these a-methylene-g-butyrolactones, using a " one-pot " Claisen-ene reaction as key-step. The study of these successive pericyclic reactions provided the desired functionalised target lactones. In the second part of our work and in order to increase the scope of our approach, the synthesis of subsituted allylsilanes has been achieved. These reagents are key intermediates in route to polysubstituted and fused bicyclic a-methylene-g-butyrolactones, close analogues to the desired natural products. Several lactones were obtained successfully, using our methodology both in inter- and intra-molecular fashion. Finally, our results led us to suggest a new transition state in order to better explain the selectivity of our ene reaction.
- Affiliations
Citations
Leclercq, C. (2006). Etude de nouvelles réactions péricycliques en cascade : application à la synthèse d’exo-méthylène-butyrolactones. https://hdl.handle.net/2078.5/129766