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dc.contributor.authorLoughlin, Wendy A
dc.contributor.authorJenkins, Ian D
dc.contributor.authorHenderson, Luke C
dc.contributor.authorCampitelli, Marc R
dc.contributor.authorHealy, Peter C
dc.date.accessioned2017-05-03T12:22:33Z
dc.date.available2017-05-03T12:22:33Z
dc.date.issued2008
dc.date.modified2009-02-10T01:42:18Z
dc.identifier.issn0022-3263
dc.identifier.doi10.1021/jo800227p
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.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.publisher.placeUnited States
dc.publisher.urihttp://pubs.acs.org/journal/joceah
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom3435
dc.relation.ispartofpageto3440
dc.relation.ispartofissue9
dc.relation.ispartofjournalJournal of Organic Chemistry
dc.relation.ispartofvolume73
dc.rights.retentionY
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchcode3404
dc.subject.fieldofresearchcode3405
dc.titleTotal Synthesis of (±)-Hyphodermins A and D
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.rights.copyright© 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.
gro.date.issued2008
gro.hasfulltextNo Full Text
gro.griffith.authorJenkins, Ian D.
gro.griffith.authorHealy, Peter C.
gro.griffith.authorLoughlin, Wendy A.


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