Synlett 1996; 1996(4): 391-392
DOI: 10.1055/s-1996-5405
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Preparation of 3-Butadienyl Tetrahydrofurans and α-Butadienyl γ-Butyrolactones by Radical Cyclization of β-Bromopent-4-en-2-ynyl Ethers and mixed Acetals

Jean-Pierre Dulcère* , Estelle Dumez1 , Robert Faure1
  • *Réactivité en Synthèse Organique, Faculté des Sciences et Techniques de St Jérôme, URA CNRS 1411, av. Esc. Normandie-Niemen, Boîte D 12, F-13397 Marseille Cedex 20
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Publication History

Publication Date:
31 December 2000 (online)

SmI2- or Bu3SnH-promoted radical carbocyclization of β-bromopent-4-en-2-ynyl ethers 1a-e and of the corresponding mixed acetals 3a,b,d,e respectively affords 3-butadienyl tetrahydrofurans 2a-e and 4a,b,d,e, which are precursors of α-butadienyl γ-butyrolactones 5a,b,d,e by oxidation.