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dc.contributor.authorLoughlin, Wendyen_US
dc.contributor.authorJenkins, Ianen_US
dc.contributor.authorHenderson, Lukeen_US
dc.contributor.authorCampitelli, Marcen_US
dc.contributor.authorHealy, Peteren_US
dc.date.accessioned2017-05-03T12:22:33Z
dc.date.available2017-05-03T12:22:33Z
dc.date.issued2008en_US
dc.date.modified2009-02-10T01:42:18Z
dc.identifier.issn00223263en_US
dc.identifier.doi10.1021/jo800227pen_AU
dc.identifier.urihttp://hdl.handle.net/10072/21244
dc.description.abstractAn efficient formal synthesis of (()-hyphodermins A and D, metabolites of Hyphoderma radula, has been completed in 12 and 11 steps, respectively. The tricyclic carbon skeleton of enone 6 was rapidly assembled from diester 11 via an R brominationn-elimination sequence followed by anhydride formation. Regioselective reduction of the lactone group of enone 6 with LiAlH(t-BuO)3 gave lactol 15. Lactol 15 was converted in two steps to (()-hyphodermin D, without the need for complex protection-deprotection strategies. Lactol 15 was converted in three steps to (()-hyphodermin A, via the key step of epoxidation of an enone in the presence of a THP lactol. A combination of NMR and ab initio studies suggests that the structures of hyphodermin C and D should be interchanged.en_US
dc.description.peerreviewedYesen_US
dc.description.publicationstatusYesen_AU
dc.languageEnglishen_US
dc.language.isoen_AU
dc.publisherAmerican Chemical Societyen_US
dc.publisher.placeUnited Statesen_US
dc.publisher.urihttp://pubs.acs.org/journal/joceahen_AU
dc.relation.ispartofstudentpublicationNen_AU
dc.relation.ispartofpagefrom3435en_US
dc.relation.ispartofpageto3440en_US
dc.relation.ispartofissue9en_US
dc.relation.ispartofjournalJournal of Organic Chemistryen_US
dc.relation.ispartofvolume73en_US
dc.rights.retentionYen_AU
dc.subject.fieldofresearchcode250301en_US
dc.titleTotal Synthesis of (±)-Hyphodermins A and Den_US
dc.typeJournal articleen_US
dc.type.descriptionC1 - Peer Reviewed (HERDC)en_US
dc.type.codeC - Journal Articlesen_US
gro.rights.copyrightCopyright 2008 American Chemical Society. Self-archiving of the author-manuscript version is not yet supported by this publisher. The contents of this journal can be freely accessed online via the ACS web page after publication. Use hypertext link above to access the ACS website.en_AU
gro.date.issued2008
gro.hasfulltextNo Full Text


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