Synthesis of the gymnodimine tetrahydrofuran core through a Ueno-Stork radical cyclization. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2011

Synthesis of the gymnodimine tetrahydrofuran core through a Ueno-Stork radical cyclization.

Sylvestre Toumieux
Redouane Beniazza
  • Fonction : Auteur
Valérie Desvergnes
Yannick Landais

Résumé

A straightforward access to the C10-C20 skeleton of gymnodimine, incorporating a tetrahydrofuran fragment, is described. The elaboration of the THF moiety is based on a stereocontrolled Ueno-Stork cyclization. A Lewis-acid mediated allylation of the resulting acetal at C13 and a Horner-Wadsworth-Emmons olefination on the ketone at C17 complete the synthesis.
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Dates et versions

hal-00586248 , version 1 (15-04-2011)

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Citer

Sylvestre Toumieux, Redouane Beniazza, Valérie Desvergnes, Rómulo Aráoz, Jordi Molgó, et al.. Synthesis of the gymnodimine tetrahydrofuran core through a Ueno-Stork radical cyclization.. Organic & Biomolecular Chemistry, 2011, 9 (10), pp.3726-32. ⟨10.1039/c1ob05240c⟩. ⟨hal-00586248⟩
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