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A chemoenzymatic route to the (+)-form of the amaryllidaceae alkaloid narseronine

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dc.contributor.authorYang, Shuxin
dc.contributor.authorBanwell, Martin
dc.contributor.authorWillis, Anthony C.
dc.contributor.authorWard, Jas S.
dc.date.accessioned2015-05-11T02:44:15Z
dc.date.available2015-05-11T02:44:15Z
dc.date.issued2014-11-03
dc.date.updated2015-12-10T09:32:22Z
dc.description.abstractThe enzymatically derived and enantiopure cis-1,2-dihydrocatechol 1 has been converted, over 14 one-pot operations, into the (+)-form of the alkaloid narseronine (2). The present study, which complements earlier work that established a route from metabolite 1 to enantiomer (–)-2, involves an N-bromosuccinimide/tri-n-butyltin hydride-mediated cyclisation reaction to construct the unsaturated B-ring lactone of the target compound.
dc.description.sponsorshipWe thank the Australian Research Council and the Institute of Advanced Studies for generous financial support.en_AU
dc.format7 pages
dc.identifier.issn0004-9425en_AU
dc.identifier.urihttp://hdl.handle.net/1885/13430
dc.publisherCSIRO Publishing
dc.rights© CSIRO 1996-2015 http://www.sherpa.ac.uk/romeo/issn/0004-9425/Author can archive pre-print (ie pre-refereeing), author can archive post-print (ie final draft post-refereeing). On author's personal repository or institutional repository. Must link to publisher version Published source must be acknowledged. (Sherpa/Romeo as of 29/7/2015). http://www.publish.csiro.au/media/client/CopyrightAssign.pdf In addition to the Author’s moral rights in respect of the Work, the Author retains the right to: Place his/her pre-publication version of the work on a personal website or institutional repository on condition that there is a link to the definitive version on the CSIRO Publishing website. (Publisher's copyright site as of 29/7/2015).
dc.sourceAustralian Journal of Chemistry
dc.subjectAlkaloids
dc.subjectCyclization
dc.subjectEnzyme activity
dc.subjectNitrogen compounds
dc.subjectAmaryllidaceae alkaloids
dc.subjectChemoenzymatic route
dc.subjectEnantiopure
dc.subjectN-bromosuccinimide
dc.subjectOne pot
dc.subjectTarget compound
dc.subjectMetabolites
dc.titleA chemoenzymatic route to the (+)-form of the amaryllidaceae alkaloid narseronine
dc.typeJournal article
dcterms.dateAccepted2014-09-07
local.bibliographicCitation.issue2en_AU
local.bibliographicCitation.lastpage247en_AU
local.bibliographicCitation.startpage241en_AU
local.contributor.affiliationYang, Shuxin, Research School of Chemistry, Institute of Advanced Studies, The Australian National Universityen_AU
local.contributor.affiliationBanwell, Martin G., Research School of Chemistry, Institute of Advanced Studies, The Australian National Universityen_AU
local.contributor.affiliationWillis, Anthony C., Research School of Chemistry, Institute of Advanced Studies, The Australian National Universityen_AU
local.contributor.affiliationWard, Jas S., Research School of Chemistry, Institute of Advanced Studies, The Australian National Universityen_AU
local.contributor.authoruidu9500594en_AU
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
local.identifier.ariespublicationu4005981xPUB885
local.identifier.citationvolume68en_AU
local.identifier.doi10.1071/CH14520en_AU
local.identifier.essn1445-0038en_AU
local.identifier.scopusID2-s2.0-84922437850
local.publisher.urlhttp://www.publish.csiro.au/en_AU
local.type.statusAccepted Versionen_AU

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