Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (-)-Trigonoliimines

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dc.contributor.authorHan, Sunkyuko
dc.contributor.authorMorrison, Karen C.ko
dc.contributor.authorHergenrother, Paul J.ko
dc.contributor.authorMovassaghi, Mohammadko
dc.date.accessioned2015-01-27T02:07:14Z-
dc.date.available2015-01-27T02:07:14Z-
dc.date.created2014-07-07-
dc.date.created2014-07-07-
dc.date.created2014-07-07-
dc.date.created2014-07-07-
dc.date.issued2014-01-
dc.identifier.citationJOURNAL OF ORGANIC CHEMISTRY, v.79, no.2, pp.473 - 486-
dc.identifier.issn0022-3263-
dc.identifier.urihttp://hdl.handle.net/10203/193063-
dc.description.abstractA full account of our concise and enantioselective total syntheses of all known (-)-trigonoliimine alkaloids is described. Our retrobiosynthetic analysis of these natural products enabled identification of a single bistryptamine precursor as a precursor to all known trigonoliimines through a sequence of transformations involving asymmetric oxidation and reorganization. Our enantioselective syntheses of these alkaloids enabled the revision of the absolute stereochemistry of (-)-trigonoliimines A, B, and C. We report that trigonoliimines A, B, C and structurally related compounds showed weak anticancer activities against HeLa and U-937 cells.-
dc.languageEnglish-
dc.publisherAMER CHEMICAL SOC-
dc.titleTotal Synthesis, Stereochemical Assignment, and Biological Activity of All Known (-)-Trigonoliimines-
dc.typeArticle-
dc.identifier.wosid000330099000001-
dc.identifier.scopusid2-s2.0-84896802062-
dc.type.rimsART-
dc.citation.volume79-
dc.citation.issue2-
dc.citation.beginningpage473-
dc.citation.endingpage486-
dc.citation.publicationnameJOURNAL OF ORGANIC CHEMISTRY-
dc.identifier.doi10.1021/jo4020358-
dc.contributor.localauthorHan, Sunkyu-
dc.contributor.nonIdAuthorMorrison, Karen C.-
dc.contributor.nonIdAuthorHergenrother, Paul J.-
dc.contributor.nonIdAuthorMovassaghi, Mohammad-
dc.description.isOpenAccessN-
dc.type.journalArticleArticle-
dc.subject.keywordPlusSTEREOCONTROLLED TOTAL-SYNTHESIS-
dc.subject.keywordPlusCONCISE TOTAL-SYNTHESIS-
dc.subject.keywordPlusENANTIOSELECTIVE EPOXIDATION-
dc.subject.keywordPlusOXIDATIVE REARRANGEMENT-
dc.subject.keywordPlusASYMMETRIC EPOXIDATION-
dc.subject.keywordPlusSTEREOSELECTIVE-SYNTHESIS-
dc.subject.keywordPlusBENZANNULATION REACTIONS-
dc.subject.keywordPlus(+/-)-TRIGONOLIIMINE C-
dc.subject.keywordPlusTRIFLUOROACETIC-ACID-
dc.subject.keywordPlusBIOMIMETIC SYNTHESIS-
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