Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses.

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.

SUBMITTER: Foster RW 

PROVIDER: S-EPMC4648048 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature