Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses |
| |
| Authors: | Robert W. Foster Dr. Christopher J. Tame Dr. Dejan‐Krešimir Bučar Prof. Helen C. Hailes Dr. Tom D. Sheppard |
| |
| Affiliation: | 1. Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London, WC1H 0AJ (UK) http://www.tomsheppard.eu;2. GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Herts, SG1 2NY (UK) |
| |
| 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. |
| |
| Keywords: | arabinose biomass hydrazines cyclization tetrahydrofurans |
|
|
