Simple and modestly scalable synthesis of iso-Cyrene from levoglucosenone and its comparison to the bio-derived and polar aprotic solvent Cyrene®

Xin Liu, Brett Pollard, Martin Banwell, Li-Juan Yu, Michelle Coote, Michael Gardiner, Barbara M A van Vugt-Lussenburg, Bart van der Burg, Fabien Grasset, Elizabeth Campillo, James Richard Sherwood, Fergal Byrne, Thomas James Farmer

Research output: Contribution to journalArticlepeer-review


The bio-derived platform molecule levoglucosenone (LGO, 1), which is the precursor to the green solvent Cyrene® (2), has been converted, at multi-gram scale, into its pseudo-enantiomer (iso-LGO, 2) and then reduced to iso-Cyrene (4). A less effective synthesis of this last compound from D-glucose is also described. Various physicochemical as well as certain toxicological properties of compound 4 are reported and compared to those established for the now commercially available Cyrene® (2). Such studies reveal that there are significant enough differences in the properties of the sustainably-derived Cyrene® (2) and isomer 4 (iso-Cyrene) to suggest they will exert complementary effects as solvents in a range of settings.
Original languageEnglish
Number of pages14
JournalAustralian Journal of Chemistry
Early online date7 Jul 2022
Publication statusE-pub ahead of print - 7 Jul 2022

Bibliographical note

© 2022 The Author(s) (or their employer(s))This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details

Cite this