Synthèse d'alcaloïdes biologiquement actifs : la (+)-anatoxine-a et la (±)-camptothécine

Abstract : The first part of this work describes a formal asymmetric synthesis of (+)-anatoxin-a, a neurotoxic alkaloid from Anabaena flos aquae. The synthetic approach is based on highly diastereoseletive [2+2] cycloaddition of dichloroketene and a chiral enol ether. Also an intramolecular cyclisation of a N-acyl iminium intermediate has been achieved in order to construct the azabicyclic core of the natural product.

In the second part, we have developped a new synthesis of racemic camptothecin. This pentacyclic alkaloid isolated from Camptotheca acuminata, was found to be a potent antitumor agent due to the inhibition of topoisomerase I. In this approach, a [3+2] cycloaddition reaction of an isomunchnone, Suzuki coupling and cyanosilylation followed by intramolecular Pinner reaction were used as key-steps.
Document type :
Theses
Other. Université Joseph-Fourier - Grenoble I, 2006. French


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Submitted on : Monday, February 5, 2007 - 5:43:09 PM
Last modification on : Monday, February 5, 2007 - 6:58:30 PM

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Mauro Neves Muniz. Synthèse d'alcaloïdes biologiquement actifs : la (+)-anatoxine-a et la (±)-camptothécine. Other. Université Joseph-Fourier - Grenoble I, 2006. French. <tel-00129103>

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