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

Yang, Shuxin; Banwell, Martin; Willis, Anthony C.; Ward, Jas S.

Description

The 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.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.identifier.issn0004-9425
dc.identifier.urihttp://hdl.handle.net/1885/13430
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.
dc.format7 pages
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
local.identifier.citationvolume68
dcterms.dateAccepted2014-09-07
dc.date.issued2014-11-03
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationu4005981xPUB885
local.publisher.urlhttp://www.publish.csiro.au/
local.type.statusAccepted Version
local.contributor.affiliationYang, Shuxin, Research School of Chemistry, Institute of Advanced Studies, The Australian National University
local.contributor.affiliationBanwell, Martin G., Research School of Chemistry, Institute of Advanced Studies, The Australian National University
local.contributor.affiliationWillis, Anthony C., Research School of Chemistry, Institute of Advanced Studies, The Australian National University
local.contributor.affiliationWard, Jas S., Research School of Chemistry, Institute of Advanced Studies, The Australian National University
local.identifier.essn1445-0038
local.bibliographicCitation.issue2
local.bibliographicCitation.startpage241
local.bibliographicCitation.lastpage247
local.identifier.doi10.1071/CH14520
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2015-12-10T09:32:22Z
local.identifier.scopusID2-s2.0-84922437850
CollectionsANU Research Publications

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