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Synlett 2000; 2000(8): 1184-1186
DOI: 10.1055/s-2000-6744
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The Synthesis of Highly Functionalised Dienes for Natural Product Synthesis

Philip J. Parsons*
  • *The Chemical Laboratories, CPES, Arundel Building, University of Sussex, Falmer, Brighton, East Sussex, BN1 9QJ, UK; Fax + 44(0)12 73 67 71 96; E-mail: P.J.Parsons@sussex.ac.uk
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Publication Date:
31 December 2000 (online)

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The Lewis acid and Bronsted acid mediated intramolecular cyclisation reactions of allenyl epoxides to 1,3-dienes are reported. Titanium(IV) chloride and hydrofluoric acid give six membered carbocyclic dienes, whereas stannic chloride affords a 2:1 mixture of six and seven membered rings respectively. Diethylaluminum chloride mediated cyclisation furnishes exclusively a seven membered ring 1,3-diene. Trimethyloxonium tetrafluoroborate gives a six membered permethylated diene.

diene - allene - cyclisation - Lewis acid - triptoquinone