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Molecular Diversity

, Volume 17, Issue 1, pp 49–53 | Cite as

3-Bromopenta-2,4-dienylsilane: a useful reagent for the preparation of [3]dendralenes and polycyclic compounds

  • Mohammed Rahif
  • Maryline Roux
  • Jérôme Thibonnet
  • Jean-Luc ParrainEmail author
Full-Length Paper

Abstract

Starting from (\(Z)\)-1-trimethylsilyl-3-bromopenta-2,4-diene, a lithium-bromine exchange reaction followed by addition onto carbonyl compounds provided the corresponding dienyl alcohols. A Peterson-type \(\gamma \)-elimination promoted by a catalytic amount of trimethylsilyl triflate cross-conjugated gave triene systems ([3]dendralene) which rapidly reacted with the appropriate dienophiles to yield tandem intermolecular Diels-Alder cycloadducts.

Keywords

Bromopentadienylsilane Dendralenes Polycycles  Tandem cycloaddition Heterocycles Diversity 

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Copyright information

© Springer Science+Business Media Dordrecht 2013

Authors and Affiliations

  • Mohammed Rahif
    • 1
  • Maryline Roux
    • 1
  • Jérôme Thibonnet
    • 2
  • Jean-Luc Parrain
    • 1
    Email author
  1. 1.Institut des Sciences Moléculaires de MarseilleAix-Marseille UniversitéMarseille Cedex 20France
  2. 2.Laboratoire d’Infectiologie et Santé Publique (UMR UFR/INRA 1282), Faculté des SciencesEquipe “Recherche et Innovation en Chimie Médicinale” Université François RabelaisToursFrance

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