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

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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.

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Authors and Affiliations

  1. Institut des Sciences Moléculaires de Marseille, Aix-Marseille Université, iSm2-UMR CNRS 6263, Campus scientifique de Saint Jérôme, Service 532, 13397 , Marseille Cedex 20, France

    Mohammed Rahif, Maryline Roux & Jean-Luc Parrain

  2. Laboratoire d’Infectiologie et Santé Publique (UMR UFR/INRA 1282), Faculté des Sciences, Equipe “Recherche et Innovation en Chimie Médicinale” Université François Rabelais, Parc de Grandmont, 37200 , Tours, France

    Jérôme Thibonnet

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  1. Mohammed Rahif
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  2. Maryline Roux
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  3. Jérôme Thibonnet
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  4. Jean-Luc Parrain
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Correspondence to Jean-Luc Parrain.

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Rahif, M., Roux, M., Thibonnet, J. et al. 3-Bromopenta-2,4-dienylsilane: a useful reagent for the preparation of [3]dendralenes and polycyclic compounds. Mol Divers 17, 49–53 (2013). https://doi.org/10.1007/s11030-012-9418-6

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  • DOI: https://doi.org/10.1007/s11030-012-9418-6

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