TY  - JOUR
JF  - Chemistry
A1  - Foster, RW
A1  - Tame, CJ
A1  - Bu?ar, DK
A1  - Hailes, HC
A1  - Sheppard, TD
SN  - 1521-3765
UR  - http://dx.doi.org/10.1002/chem.201503510
N1  - © 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.
IS  - 45
VL  - 21
SP  - 15947
KW  - arabinose
KW  -  biomass
KW  -  cyclization
KW  -  hydrazines
KW  -  tetrahydrofurans
ID  - discovery1472231
N2  - 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.
TI  - Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses
EP  - 15950
AV  - public
Y1  - 2015/11/02/
ER  -