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Total Syntheses of the Amaryllidaceae Alkaloids Zephycandidine III and Lycosinine A and Their Evaluation as Inhibitors of Acetylcholinesterase

Xu, Xingjun; Kim, Hye; Chen, Weimin; Ma, Xiang; Correy, Galen; Banwell, Martin; Jackson, Colin; Willis, Anthony; Carr, Paul D

Description

The title alkaloids, 1 and 2, have been prepared using cross-coupling chemistries and together with various analogues they have been evaluated for their capacity to inhibit acetylcholinesterase. Contrary to an earlier report, it was found that biaryl 1 is not a significant inhibitor of this enzyme, and neither are any of its congeners, including alkaloid 2.

dc.contributor.authorXu, Xingjun
dc.contributor.authorKim, Hye
dc.contributor.authorChen, Weimin
dc.contributor.authorMa, Xiang
dc.contributor.authorCorrey, Galen
dc.contributor.authorBanwell, Martin
dc.contributor.authorJackson, Colin
dc.contributor.authorWillis, Anthony
dc.contributor.authorCarr, Paul D
dc.date.accessioned2019-04-08T03:57:46Z
dc.identifier.issn1434-193X
dc.identifier.urihttp://hdl.handle.net/1885/159300
dc.description.abstractThe title alkaloids, 1 and 2, have been prepared using cross-coupling chemistries and together with various analogues they have been evaluated for their capacity to inhibit acetylcholinesterase. Contrary to an earlier report, it was found that biaryl 1 is not a significant inhibitor of this enzyme, and neither are any of its congeners, including alkaloid 2.
dc.description.sponsorshipWe thank Jinan University, the Australian Research Council, and the Institute of Advanced Studies for financial support. H. S. K. and G. J. C. are the grateful recipients of scholarships provided by the Australian Government.
dc.format.extent10 pages
dc.format.mimetypeapplication/pdf
dc.language.isoen_AU
dc.publisherWiley-VCH Verlag GMBH
dc.rights© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
dc.sourceEuropean Journal of Organic Chemistry
dc.subjectAChE inhibition
dc.subjectAlkaloids
dc.subjectBiaryls
dc.subjectCross coupling
dc.subjectLycosinine A
dc.subjectZephycandidine III
dc.titleTotal Syntheses of the Amaryllidaceae Alkaloids Zephycandidine III and Lycosinine A and Their Evaluation as Inhibitors of Acetylcholinesterase
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume2017
dc.date.issued2017
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationa383154xPUB7520
local.publisher.urlhttps://www.wiley.com/en-gb
local.type.statusAccepted Version
local.contributor.affiliationXu, Xingjun, College of Science, The Australian National University
local.contributor.affiliationKim, Hye, College of Science, The Australian National University
local.contributor.affiliationChen, Weimin, Jinan University
local.contributor.affiliationMa, Xiang, College of Science, The Australian National University
local.contributor.affiliationCorrey, Galen, College of Science, The Australian National University
local.contributor.affiliationBanwell, Martin, College of Science, The Australian National University
local.contributor.affiliationJackson, Colin, College of Science, The Australian National University
local.contributor.affiliationWillis, Anthony, College of Science, The Australian National University
local.contributor.affiliationCarr, Paul D, College of Science, The Australian National University
dc.relationhttp://purl.org/au-research/grants/arc/DP170100926
local.identifier.essn1099-0690
local.bibliographicCitation.issue27
local.bibliographicCitation.startpage4044
local.bibliographicCitation.lastpage4053
local.identifier.doi10.1002/ejoc.201700705
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2019-03-12T07:20:57Z
local.identifier.scopusID2-s2.0-85025650780
dcterms.accessRightsOpen Access
dc.provenancehttp://sherpa.mimas.ac.uk/romeo/issn/1434-193X/ Author can archive pre-print (ie pre-refereeing). author can archive post-print (ie final draft post-refereeing) with a 12 months embargo (Sherpa/Romeo as of 8/4/2019)
dc.provenancehttps://v2.sherpa.ac.uk/id/publication/1692..."The Accepted Version can be archived in a Non-Commercial Institutional Repository. 12 months embargo" from SHERPA/RoMEO site (as at 6/01/2021). This is the peer reviewed version of the following article: [Xu, Xingjun, et al. "Total Syntheses of the Amaryllidaceae alkaloids zephycandidine III and lycosinine A and their evaluation as inhibitors of acetylcholinesterase." European Journal of Organic Chemistry 2017.27 (2017): 4044-4053.], which has been published in final form at https://dx.doi.org/10.1002/ejoc.201700705. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
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