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Publication Detail
Irreversible endo-Selective Diels-Alder Reactions of Substituted Alkoxyfurans: A General Synthesis of endo-Cantharimides
  • Publication Type:
    Journal article
  • Publication Sub Type:
    Journal Article
  • Authors:
    Foster RW, Benhamou L, Porter MJ, Bučar DK, Hailes HC, Tame CJ, Sheppard TD
  • Publication date:
    13/04/2015
  • Pagination:
    6107, 6114
  • Journal:
    Chemistry - A European Journal
  • Volume:
    21
  • Issue:
    16
  • Status:
    Published
  • Print ISSN:
    0947-6539
Abstract
© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. The [4+2] cycloaddition of 3-alkoxyfurans with N-substituted maleimides provides the first general route for preparing endo-cantharimides. Unlike the corresponding reaction with 3H furans, the reaction can tolerate a broad range of 2-substitued furans including alkyl, aromatic, and heteroaromatic groups. The cycloaddition products were converted into a range of cantharimide products with promising lead-like properties for medicinal chemistry programs. Furthermore, the electron-rich furans are shown to react with a variety of alternative dienophiles to generate 7-oxabicyclo[2.2.1]heptane derivatives under mild conditions. DFT calculations have been performed to rationalize the activation effect of the 3-alkoxy group on a furan Diels-Alder reaction.
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