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.
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Authors | Robert W Foster, Christopher J Tame, Dejan-Krešimir Bučar, Helen C Hailes, Tom D Sheppard |
Journal | Chemistry (Weinheim an der Bergstrasse, Germany)
(Chemistry)
Vol. 21
Issue 45
Pg. 15947-50
(Nov 02 2015)
ISSN: 1521-3765 [Electronic] Germany |
PMID | 26407081
(Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
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Copyright | © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
Chemical References |
- 3-hydroxymuscarine
- Furans
- Hydrazones
- Pentoses
- Muscarine
- Arabinose
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Topics |
- Arabinose
(chemistry)
- Cyclization
- Dehydration
- Furans
(chemistry)
- Hydrazones
(chemistry)
- Muscarine
(analogs & derivatives, chemical synthesis, chemistry)
- Pentoses
(chemical synthesis, chemistry)
- Stereoisomerism
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