A Total Synthesis of (±)-3-O-Demethylmacronine through Rearrangement of a Precursor Embodying the Haemanthidine Alkaloid Framework

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dc.contributor.authorMa, Xiang
dc.contributor.authorGao, Yuqian (Nadia)
dc.contributor.authorBanwell, Martin
dc.contributor.authorCarr, Paul D
dc.contributor.authorWillis, Anthony
dc.date.accessioned2021-01-06T04:03:48Z
dc.date.available2021-01-06T04:03:48Z
dc.date.issued2017
dc.date.updated2020-11-23T10:08:34Z
dc.description.abstractA total synthesis of the racemic modification, (±)-2, of the tazettine-type alkaloid 3-O-demethylmacronine is described. The key steps are an intramolecular Alder-ene (IMAE) reaction and a lactam-to-lactone rearrangement of tetracycle 13, a compound that embodies the haemanthidine alkaloid framework.en_AU
dc.description.sponsorshipWe thank the Australian Research Council for financial support. X.M. is the grateful recipient of a PhD Scholarship provided by the Guangzhou Elite Project of the Guangzhou Municipal Government, People’ s Republic of China.en_AU
dc.format.mimetypeapplication/pdfen_AU
dc.identifier.issn0022-3263en_AU
dc.identifier.urihttp://hdl.handle.net/1885/219195
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 5/01/2021). 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.7b00340en_AU
dc.publisherAmerican Chemical Societyen_AU
dc.relationhttp://purl.org/au-research/grants/arc/DP170100926en_AU
dc.rights© 2017 American Chemical Societyen_AU
dc.sourceJournal of Organic Chemistryen_AU
dc.titleA Total Synthesis of (±)-3-O-Demethylmacronine through Rearrangement of a Precursor Embodying the Haemanthidine Alkaloid Frameworken_AU
dc.typeJournal articleen_AU
dcterms.accessRightsOpen Accessen_AU
local.bibliographicCitation.issue8en_AU
local.bibliographicCitation.lastpage4341en_AU
local.bibliographicCitation.startpage4336en_AU
local.contributor.affiliationMa, Xiang, College of Science, ANUen_AU
local.contributor.affiliationGao, Yuqian (Nadia), College of Science, ANUen_AU
local.contributor.affiliationBanwell, Martin, College of Science, ANUen_AU
local.contributor.affiliationCarr, Paul D, College of Science, ANUen_AU
local.contributor.affiliationWillis, Anthony, College of Science, ANUen_AU
local.contributor.authoremailmartin.banwell@anu.edu.auen_AU
local.contributor.authoruidMa, Xiang, u5342100en_AU
local.contributor.authoruidGao, Yuqian (Nadia), u4372102en_AU
local.contributor.authoruidBanwell, Martin, u9500594en_AU
local.contributor.authoruidCarr, Paul D, u9206448en_AU
local.contributor.authoruidWillis, Anthony, u8512028en_AU
local.description.notesImported from ARIESen_AU
local.identifier.absfor030503 - Organic Chemical Synthesisen_AU
local.identifier.ariespublicationa383154xPUB5834en_AU
local.identifier.citationvolume82en_AU
local.identifier.doi10.1021/acs.joc.7b00340en_AU
local.identifier.scopusID2-s2.0-85018464587
local.identifier.thomsonID000400124100031
local.identifier.uidSubmittedBya383154en_AU
local.publisher.urlhttp://pubs.acs.org/journal/joceah/about.htmlen_AU
local.type.statusAccepted Versionen_AU

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