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dc.contributor.authorHenderson, LC
dc.contributor.authorLoughlin, WA
dc.contributor.authorJenkins, ID
dc.contributor.authorHealy, PC
dc.contributor.authorCampitelli, MR
dc.contributor.editorC. Dale Poulter
dc.date.accessioned2017-05-03T11:07:35Z
dc.date.available2017-05-03T11:07:35Z
dc.date.issued2006
dc.date.modified2008-11-21T03:21:25Z
dc.identifier.issn0022-3263
dc.identifier.doi10.1021/jo052485l
dc.identifier.urihttp://hdl.handle.net/10072/13871
dc.description.abstractAn efficient formal synthesis of hyphodermin B 1, a metabolite of Hyphoderma radula, has been completed in 15% overall yield. The tricyclic carbon skeleton 3 was rapidly assembled from a novel vinyl enone via a Diels-Alder reaction, followed by dehydrogenation and anhydride formation. Selective reduction of anhydride 3 with LiAlH(t-BuO)3 gave hyphodermin B 1 in 99% yield. The structure of hyphodermin B 1 was confirmed by X-ray crystallographic analysis. The anhydride 3, bearing a ?-carbonyl group, displayed unexpected reactivity with the anhydride carbonyl closest to the ?-ketone being the most electrophilic site. This was confirmed by HF/6-31G* calculations. In the presence of base, 3 underwent a rearrangement to the novel lactone 16.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.publisher.placeUSA
dc.publisher.urihttp://pubs.acs.org/journal/joceah
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom2384
dc.relation.ispartofpageto2388
dc.relation.ispartofedition2006
dc.relation.ispartofissue6
dc.relation.ispartofjournalJournal of Organic Chemistry
dc.relation.ispartofvolume71
dc.rights.retentionY
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchcode3404
dc.subject.fieldofresearchcode3405
dc.titleEfficient formal synthesis of (±)-Hyphodermin B
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.facultyGriffith Sciences, Griffith Institute for Drug Discovery
gro.rights.copyright© 2006 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.
gro.date.issued2006
gro.hasfulltextNo Full Text
gro.griffith.authorJenkins, Ian D.
gro.griffith.authorHealy, Peter C.
gro.griffith.authorLoughlin, Wendy A.


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