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Establishing the True Structure of the Sorbicillinoid-Derived Isolate Rezishanone C by Total Synthesis

Yan, Qiao; Banwell, Martin; Coote, Michelle; Lee, Zhong (Richmond); Willis, Anthony

Description

The enantiomer, ent-4, of the true structure, 4, of the sorbicillinoid rezishanone C (sorbivinetone) has been synthesized from a homochiral cis-1,2-dihydrocatechol that is itself generated through the whole-cell biotransformation of toluene. These studies together with dispersion-corrected DFT calculations support the proposal that rezishanone C is an artefact of the isolation process and arises through a Diels-Alder reaction between ethyl vinyl ether and sorbicillinol (3).

dc.contributor.authorYan, Qiao
dc.contributor.authorBanwell, Martin
dc.contributor.authorCoote, Michelle
dc.contributor.authorLee, Zhong (Richmond)
dc.contributor.authorWillis, Anthony
dc.date.accessioned2019-04-08T02:03:24Z
dc.identifier.issn1861-4728
dc.identifier.urihttp://hdl.handle.net/1885/159289
dc.description.abstractThe enantiomer, ent-4, of the true structure, 4, of the sorbicillinoid rezishanone C (sorbivinetone) has been synthesized from a homochiral cis-1,2-dihydrocatechol that is itself generated through the whole-cell biotransformation of toluene. These studies together with dispersion-corrected DFT calculations support the proposal that rezishanone C is an artefact of the isolation process and arises through a Diels-Alder reaction between ethyl vinyl ether and sorbicillinol (3).
dc.format.mimetypeapplication/pdf
dc.language.isoen_AU
dc.publisherWiley-VCH Verlag GMBH
dc.sourceChemistry - An Asian Journal
dc.titleEstablishing the True Structure of the Sorbicillinoid-Derived Isolate Rezishanone C by Total Synthesis
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume12
dc.date.issued2017
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationa383154xPUB6445
local.type.statusPublished Version
local.contributor.affiliationYan, Qiao, College of Science, ANU
local.contributor.affiliationBanwell, Martin, College of Science, ANU
local.contributor.affiliationCoote, Michelle, College of Science, ANU
local.contributor.affiliationLee, Zhong (Richmond), College of Science, ANU
local.contributor.affiliationWillis, Anthony, College of Science, ANU
local.description.embargo2039-12-31
local.bibliographicCitation.issue13
local.identifier.doi10.1002/asia.201700456
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2019-03-12T07:20:44Z
local.identifier.scopusID2-s2.0-85020183731
local.identifier.thomsonID000405717500011
dc.provenanceJournal: Chemistry - An Asian Journal (ISSN: 1861-4728, ESSN: 1861-471X) RoMEO: This is a RoMEO yellow journal Paid OA: A paid open access option is available for this journal. Author's Pre-print: green tick author can archive pre-print (ie pre-refereeing) Author's Post-print: grey tick subject to Restrictions below, author can archive post-print (ie final draft post-refereeing) Restrictions: 12 months embargo Publisher's Version/PDF: cross author cannot archive publisher's version/PDF
CollectionsANU Research Publications

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