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Synlett 2000; 2000(2): 260-262
DOI: 10.1055/s-2000-6485
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Halolactonisation of (2Z,4E)-dienoic Acids. A Novel Approach to γ-Alkylidene Butenolides

Séverine Rousset* , Jérôme Thibonnet, Mohamed Abarbri, Alain Duchêne, Jean-Luc Parrain
  • *Laboratoire de Physicochimie des Interfaces et des Milieux Réactionnels, Faculté des Sciences de Tours, Parc de Grandmont, 37200 Tours, France; E-mail: duchene@delphi.phys.univ-tours.fr
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Publikationsdatum:
31. Dezember 2000 (online)

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Stereoselective synthesis of alkylidene butenolides was achieved from (2Z,4E)-dienoic acids by a sequence involving halocyclisation and elimination reactions. Selectivity was found to be highly dependent on the nature of the substituents. This methodology has been applied to the synthesis of a retinoid containing the alkylidene butenolide core.

halolactonisation - elimination reaction - dienoic acids - butenolides - γ-alkylidene butenolides