@article{discovery1472231, pages = {15947--15950}, note = {{\copyright} 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.}, volume = {21}, journal = {Chemistry}, title = {Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses}, year = {2015}, number = {45}, month = {November}, 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.}, issn = {1521-3765}, author = {Foster, RW and Tame, CJ and Bu{\vc}ar, DK and Hailes, HC and Sheppard, TD}, url = {http://dx.doi.org/10.1002/chem.201503510}, keywords = {arabinose, biomass, cyclization, hydrazines, tetrahydrofurans} }