Premium
Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses
Author(s) -
Foster Robert W.,
Tame Christopher J.,
Bučar DejanKrešimir,
Hailes Helen C.,
Sheppard Tom D.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503510
Subject(s) - hydrazone , chemistry , tetrahydrofuran , arabinose , formal synthesis , sugar , organic chemistry , combinatorial chemistry , solvent , fermentation , xylose
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 3 R ‐3‐hydroxymuscarine.