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Synthesis of a Highly Functionalised and Homochiral 2-Iodocyclohexenone Related to the C-Ring of the Polycyclic, Indole Alkaloids Aspidophytine and Haplophytine

Dlugosch, Michael; Banwell, Martin

Description

The enzymatically-derived and enantiomerically pure (1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol (7) has been elaborated over 10 steps into cyclohexenone 8. The latter compound embodies the enantiomeric form of the C-ring associated with the hexacyclic framework of the alkaloid aspidophytine (2). As such, this work sets the stage for effecting the conversion of the enantiomeric metabolite ent-7 into compound ent-8, and thence, through previously established protocols, including a...[Show more]

dc.contributor.authorDlugosch, Michael
dc.contributor.authorBanwell, Martin
dc.date.accessioned2019-04-21T12:04:16Z
dc.identifier.issn0004-9425
dc.identifier.urihttp://hdl.handle.net/1885/160587
dc.description.abstractThe enzymatically-derived and enantiomerically pure (1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol (7) has been elaborated over 10 steps into cyclohexenone 8. The latter compound embodies the enantiomeric form of the C-ring associated with the hexacyclic framework of the alkaloid aspidophytine (2). As such, this work sets the stage for effecting the conversion of the enantiomeric metabolite ent-7 into compound ent-8, and thence, through previously established protocols, including a palladium-catalysed Ullmann cross-coupling reaction, into the title alkaloids.
dc.format.mimetypeapplication/pdf
dc.language.isoen_AU
dc.publisherCSIRO Publishing
dc.sourceAustralian Journal of Chemistry
dc.titleSynthesis of a Highly Functionalised and Homochiral 2-Iodocyclohexenone Related to the C-Ring of the Polycyclic, Indole Alkaloids Aspidophytine and Haplophytine
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume71
dc.date.issued2018
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationu4485658xPUB2364
local.type.statusAccepted Version
local.contributor.affiliationDlugosch, Michael, College of Science, ANU
local.contributor.affiliationBanwell, Martin, College of Science, ANU
dc.relationhttp://purl.org/au-research/grants/arc/DP150101947
local.bibliographicCitation.issue8
local.identifier.doi10.1071/CH18267
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2019-03-12T07:34:10Z
local.identifier.thomsonID000445007000004
dcterms.accessRightsOpen Access
dc.provenancehttps://v2.sherpa.ac.uk/id/publication/7669..."The Accepted Version can be archived in Institutional Repository" from SHERPA/RoMEO site (as at 7/01/2021).
CollectionsANU Research Publications

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