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Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses.

Abstract
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.
AuthorsRobert W Foster, Christopher J Tame, Dejan-Krešimir Bučar, Helen C Hailes, Tom D Sheppard
JournalChemistry (Weinheim an der Bergstrasse, Germany) (Chemistry) Vol. 21 Issue 45 Pg. 15947-50 (Nov 02 2015) ISSN: 1521-3765 [Electronic] Germany
PMID26407081 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Copyright© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Chemical References
  • 3-hydroxymuscarine
  • Furans
  • Hydrazones
  • Pentoses
  • Muscarine
  • Arabinose
Topics
  • Arabinose (chemistry)
  • Cyclization
  • Dehydration
  • Furans (chemistry)
  • Hydrazones (chemistry)
  • Muscarine (analogs & derivatives, chemical synthesis, chemistry)
  • Pentoses (chemical synthesis, chemistry)
  • Stereoisomerism

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