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Accessing Polyoxygenated Dibenzofurans via the Union of Phenols and o-Benzoquinones: Rapid Syntheses of Metabolites Isolated from Ribes takare

Zhang, Meng; Barrow, Russell

Description

The construction of polyoxygenated dibenzo[b,d]furan frameworks from the union of substituted phenols/naphthols and o-benzoquinones via a Michael-oxidation-oxa-Michael cascade is reported. The power of this transformation is demonstrated in the generation of a library of highly substituted dibenzofurans, featuring specifically substituted molecules containing broad ranges of functionality. The utility of this method is showcased in the total syntheses of two dibenzofurans isolated from Ribes...[Show more]

dc.contributor.authorZhang, Meng
dc.contributor.authorBarrow, Russell
dc.date.accessioned2019-04-08T02:28:02Z
dc.identifier.issn1523-7060
dc.identifier.urihttp://hdl.handle.net/1885/159296
dc.description.abstractThe construction of polyoxygenated dibenzo[b,d]furan frameworks from the union of substituted phenols/naphthols and o-benzoquinones via a Michael-oxidation-oxa-Michael cascade is reported. The power of this transformation is demonstrated in the generation of a library of highly substituted dibenzofurans, featuring specifically substituted molecules containing broad ranges of functionality. The utility of this method is showcased in the total syntheses of two dibenzofurans isolated from Ribes takare, assembling the carbon scaffold of both natural products in one operation.
dc.format.mimetypeapplication/pdf
dc.language.isoen_AU
dc.publisherAmerican Chemical Society
dc.sourceOrganic Letters
dc.titleAccessing Polyoxygenated Dibenzofurans via the Union of Phenols and o-Benzoquinones: Rapid Syntheses of Metabolites Isolated from Ribes takare
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume19
dc.date.issued2017
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationa383154xPUB7003
local.type.statusPublished Version
local.contributor.affiliationZhang, Meng, College of Science, ANU
local.contributor.affiliationBarrow, Russell, College of Science, ANU
local.description.embargo2039-12-31
local.bibliographicCitation.issue9
local.identifier.doi10.1021/acs.orglett.7b00840
dc.date.updated2019-03-12T07:20:54Z
local.identifier.scopusID2-s2.0-85019047658
local.identifier.thomsonID000401044500027
dc.provenanceJournal: Organic Letters (ISSN: 1523-7060, ESSN: 1523-7052) RoMEO: This is a RoMEO white journal Paid OA: A paid open access option is available for this journal. Author's Pre-print: grey tick subject to Restrictions below, author can archive pre-print (ie pre-refereeing) Restrictions: Must obtain written permission from Editor Must not violate ACS ethical Guidelines Author's Post-print: grey tick subject to Restrictions below, author can archive post-print (ie final draft post-refereeing) Restrictions: If mandated by funding agency or employer/ institution If mandated to deposit before 12 months, must obtain waiver from Institution/Funding agency or use AuthorChoice 12 months embargo Publisher's Version/PDF: cross author cannot archive publisher's
CollectionsANU Research Publications

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