Foster, RW;
Tame, CJ;
Bučar, DK;
Hailes, HC;
Sheppard, TD;
(2015)
Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses.
Chemistry
, 21
(45)
pp. 15947-15950.
10.1002/chem.201503510.
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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.
| Type: | Article |
|---|---|
| Title: | Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses |
| Location: | Germany |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1002/chem.201503510 |
| Publisher version: | http://dx.doi.org/10.1002/chem.201503510 |
| Additional information: | © 2015 The Authors. Published by Wiley-VCH Verlag GmbH &Co. KGaA, Weinheim. This is an open access article under the terms of the Creative Commons At- tributionLicense, whichpermits use, distributionand reproduction in any medium, provided the original work is properly cited. |
| Keywords: | arabinose, biomass, cyclization, hydrazines, tetrahydrofurans |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/1472231 |
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