Open Research will be updating the system on Tuesday, 14 July 2026, from 8:15 to 9:00 AM. We apologise for any inconvenience caused.

Cultural advice

The Australian National University acknowledges, celebrates and pays our respects to the Ngunnawal and Ngambri people of the Canberra region and to all First Nations Australians on whose traditional lands we meet and work, and whose cultures are among the oldest continuing cultures in human history.

Aboriginal and Torres Strait Islander peoples are advised that ANU Library collections may include images, names, voices, and other representations of deceased persons.

Material in the collection may contain terms, language or views that reflect the period in which the item was created and may be considered inappropriate today.

The conversion of levoglucosenone into isolevoglucosenone

Simple item page
dc.contributor.authorMa, Xinghua
dc.contributor.authorAnderson, Natasha
dc.contributor.authorWhite, Lorenzo
dc.contributor.authorBae, Song
dc.contributor.authorRaverty, Warwick
dc.contributor.authorWillis, Anthony
dc.contributor.authorBanwell, Martin
dc.date.accessioned2015-12-10T23:24:45Z
dc.date.issued2015
dc.date.updated2015-12-10T10:49:54Z
dc.description.abstractLevoglucosenone (1), a compound that will soon be available in tonne quantities through the pyrolysis of acid-treated lignocellulosic biomass, has been converted into isolevoglucosenone (2) using Wharton rearrangement chemistry. Treatment of compound 1 with alkaline hydrogen peroxide gave the γ-lactones 5 and 6 rather than the required epoxy-ketones 3 and/or 4. However, the latter pair of compounds could be obtained by an initial Luche reduction of compound 1, electrophilic epoxidation of the resulting allylic alcohol 8 and oxidation of the product oxiranes 9 and 10. Independent treatment of compounds 3 and 4 with hydrazine then acetic acid followed by oxidation of the ensuing allylic alcohols finally afforded isolevoglucosenone (2). Details of the single-crystal X-ray analyses of epoxy-alcohols 9 and 10 are reported.
dc.identifier.issn0004-9425
dc.identifier.urihttp://hdl.handle.net/1885/67335
dc.publisherCSIRO Publishing
dc.sourceAustralian Journal of Chemistry
dc.titleThe conversion of levoglucosenone into isolevoglucosenone
dc.typeJournal article
local.bibliographicCitation.issue4
local.bibliographicCitation.lastpage599
local.bibliographicCitation.startpage593
local.contributor.affiliationMa, Xinghua, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationAnderson, Natasha, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationWhite, Lorenzo, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationBae, Song, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationRaverty, Warwick, Circa Group Pty Ltd
local.contributor.affiliationWillis, Anthony, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationBanwell, Martin, College of Physical and Mathematical Sciences, ANU
local.contributor.authoruidMa, Xinghua, u4002198
local.contributor.authoruidAnderson, Natasha, u5015615
local.contributor.authoruidWhite, Lorenzo, u4213207
local.contributor.authoruidBae, Song, u5475304
local.contributor.authoruidWillis, Anthony, u8512028
local.contributor.authoruidBanwell, Martin, u9500594
local.description.embargo2037-12-31
local.description.notesImported from ARIES
local.identifier.absfor030502 - Natural Products Chemistry
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
local.identifier.ariespublicationa383154xPUB1439
local.identifier.citationvolume68
local.identifier.doi10.1071/CH14574
local.identifier.scopusID2-s2.0-84927772379
local.type.statusPublished Version

Downloads

Original bundle

Now showing 1 - 1 of 1
Thumbnail Image
Name:
01_Ma_The_conversion_of_2015.pdf
Size:
554.83 KB
Format:
Adobe Portable Document Format
Download

Collections

ANU Research Publications

DSpace software copyright © 2002-2026 LYRASIS

abcd