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Total Synthesis of (+)-Viridianol, a Marine-Derived Sesquiterpene Embodying the Decahydrocyclobuta[ d]indene Framework

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dc.contributor.authorTang, Fei
dc.contributor.authorLan, Ping
dc.contributor.authorBolte, Benoit
dc.contributor.authorBanwell, Martin
dc.contributor.authorWard, Jas
dc.contributor.authorWillis, Anthony
dc.date.accessioned2020-02-10T01:20:48Z
dc.date.issued2018-10-25
dc.date.updated2019-11-25T07:30:36Z
dc.description.abstractA total synthesis of the title sesquiterpene 4 is described that starts with the chiral, non-racemic cis-1,2-dihydrocatechol 10 obtained through the whole-cell biotransformation of p-iodotoluene. Compound 10 is elaborated over seven steps, including Negishi cross-coupling and intramolecular Diels–Alder (IMDA) cycloaddition reactions, to ketone 7 that engages in a photochemically promoted 1,3-acyl migration and so affording cyclobutanone 6. Compound 6 was converted over further steps into the title compound 4.en_AU
dc.description.sponsorshipWe thank the Australian Research Council and the Institute of Advanced Studies for financial support. F.T. and P.L. are the grateful recipients of funding provided by the CSC of the Government of the People’s Republic of China.en_AU
dc.format.extent8 pagesen_AU
dc.format.mimetypeapplication/pdfen_AU
dc.identifier.issn0022-3263en_AU
dc.identifier.urihttp://hdl.handle.net/1885/201573
dc.language.isoen_AUen_AU
dc.provenancehttps://v2.sherpa.ac.uk/id/publication/7797..."The Accepted Version can be archived in a Non-Commercial Institutional Repository If Required by Funder, If Required by Institution. 12 months embargo " from SHERPA/RoMEO site (as at 7/01/2021). This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://dx.doi.org/10.1021/acs.joc.8b02626
dc.publisherAmerican Chemical Societyen_AU
dc.relationhttp://purl.org/au-research/grants/arc/DP150101947
dc.rights© 2018 American Chemical Societyen_AU
dc.sourceJournal of Organic Chemistryen_AU
dc.titleTotal Synthesis of (+)-Viridianol, a Marine-Derived Sesquiterpene Embodying the Decahydrocyclobuta[ d]indene Frameworken_AU
dc.typeJournal articleen_AU
dcterms.accessRightsOpen Access
local.bibliographicCitation.issue22en_AU
local.bibliographicCitation.lastpage14056en_AU
local.bibliographicCitation.startpage14049en_AU
local.contributor.affiliationTang, Fei, College of Science, The Australian National Universityen_AU
local.contributor.affiliationLan, Ping, College of Science, The Australian National Universityen_AU
local.contributor.affiliationBolte, Benoit, College of Science, The Australian National Universityen_AU
local.contributor.affiliationBanwell, Martin, College of Science, The Australian National Universityen_AU
local.contributor.affiliationWard, James, College of Science, The Australian National Universityen_AU
local.contributor.affiliationWillis, Anthony, College of Science, The Australian National Universityen_AU
local.contributor.authoruidTang, Fei, u5519741en_AU
local.contributor.authoruidLan, Ping, u4986713en_AU
local.contributor.authoruidBolte, Benoit, u5403288en_AU
local.contributor.authoruidBanwell, Martin, u9500594en_AU
local.contributor.authoruidWard, James, u4431856en_AU
local.contributor.authoruidWillis, Anthony, u8512028en_AU
local.description.notesImported from ARIESen_AU
local.identifier.absfor039904 - Organometallic Chemistryen_AU
local.identifier.absfor030207 - Transition Metal Chemistryen_AU
local.identifier.absfor030204 - Main Group Metal Chemistryen_AU
local.identifier.absseo970102 - Expanding Knowledge in the Physical Sciencesen_AU
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciencesen_AU
local.identifier.ariespublicationu3102795xPUB1388en_AU
local.identifier.citationvolume83en_AU
local.identifier.doi10.1021/acs.joc.8b02626en_AU
local.identifier.essn1520-6904en_AU
local.identifier.scopusID2-s2.0-85056555739
local.publisher.urlhttps://pubs.acs.org/en_AU
local.type.statusAccepted Versionen_AU

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