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Publication Detail
Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses
  • Publication Type:
    Journal article
  • Publication Sub Type:
    Journal Article
  • Authors:
    Foster RW, Tame CJ, Bučar DK, Hailes HC, Sheppard TD
  • Publication date:
    01/11/2015
  • Pagination:
    15947, 15950
  • Journal:
    Chemistry - A European Journal
  • Volume:
    21
  • Issue:
    45
  • Status:
    Published
  • Print ISSN:
    0947-6539
Abstract
© 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.L-Arabinose is an abundant resource available as a waste product of the sugar beet industry. Through use of a hydrazone-based strategy, L-arabinose was selectively dehydrated to form a chiral tetrahydrofuran on a multi-gram scale without the need for protecting groups. This approach was extended to other biomass-derived reducing sugars and the mechanism of the key cyclization investigated. This methodology was applied to the synthesis of a range of functionalized chiral tetrahydrofurans, as well as a formal synthesis of 3R-3-hydroxymuscarine.
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