Recycling Mitsunobu coupling: a shortcut for troublesome esterifications

Boudjema Menhour 1 Firmin Obounou Akong 1 Patrick Mayon 1 Karen Plé 2 Sandrine Bouquillon 1 Stephan Dorey 3 Christophe Clément 4 Magali Deleu 5 Dominique Harakat 1 Arnaud Haudrechy 1
1 ICMR - Institut de Chimie Moléculaire de Reims - UMR 7312
2 ICOA - Institut de Chimie Organique et Analytique
3 RIBP - Résistance Induite et Bioprotection des Plantes - EA 4707
4 URVVC - Unité de Recherche Vigne et Vins de Champagne Stress et Environnement - EA 4707
5 Université de Liège
Abstract : An unusual recycling Mitsunobu reaction proved to be successful to couple two fragments in the course of the synthesis of the hydrophobic moiety of rhamnolipid derivatives. Based on the obtained pivotal intermediate, a one pot ‘cross-metathesis/reduction’ approach gave access to structural variations of the side chains. Further study of these molecules will contribute to a better understanding of the role of the lipid moiety in immunostimulatory and plant defense eliciting properties.
Keywords : Mitsunobu reaction Rhamnolipids One-pot two-step cross-metathesisreduction
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Journal articles
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Submitted on : Thursday, July 5, 2018 - 4:47:05 PM
Last modification on : Thursday, December 12, 2019 - 9:58:38 AM

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Boudjema Menhour, Firmin Obounou Akong, Patrick Mayon, Karen Plé, Sandrine Bouquillon, et al.. Recycling Mitsunobu coupling: a shortcut for troublesome esterifications. Tetrahedron, Elsevier, 2016, 72 (47), pp.7488 - 7495. ⟨10.1016/j.tet.2016.09.065⟩. ⟨hal-01831189⟩

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