Biosynthetically Inspired Syntheses of Secu′amamine A and Fluvirosaones A and B

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dc.contributor.authorLee, Sanghyeonko
dc.contributor.authorKang, Gyuminko
dc.contributor.authorChung, Garamko
dc.contributor.authorKim, Dongwookko
dc.contributor.authorLee, Hee-Yoonko
dc.contributor.authorHan, Sunkyuko
dc.date.accessioned2020-04-14T07:20:15Z-
dc.date.available2020-04-14T07:20:15Z-
dc.date.created2020-04-14-
dc.date.created2020-04-14-
dc.date.issued2020-04-
dc.identifier.citationANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.59, no.17, pp.6894 - 6901-
dc.identifier.issn1433-7851-
dc.identifier.urihttp://hdl.handle.net/10203/273891-
dc.description.abstractPresented here is a concise synthesis of secu ' amamine A, and fluvirosaones A and B from readily available allosecurinine and viroallosecurinine. The key C2-enamine derivative of (viro)allosecurinine, the presumed biosynthetic precursors of these natural products, was accessed, for the first time, by a VO(acac)(2)-mediated regioselective Polonovski reaction. Formal hydration and 1,2-amine shift of this pluripotent enamine compound afforded secu ' amamine A. Formal oxidative [3+2] cycloaddition reaction between this enamine and TMS-substituted methallyl iodide reagent paved the way to the precursors of fluvirosaones A and B. The relative stereochemistry at the C2 position of these advanced intermediates governs the fate of 1,2-amine shift leading to fluvirosaones A and B. The syntheses of potential biosynthetic precursors and investigations of their chemical reactivities have provided insights regarding the biogenesis of these natural products.-
dc.languageEnglish-
dc.publisherWILEY-V C H VERLAG GMBH-
dc.titleBiosynthetically Inspired Syntheses of Secu′amamine A and Fluvirosaones A and B-
dc.typeArticle-
dc.identifier.wosid000525279800039-
dc.identifier.scopusid2-s2.0-85081257277-
dc.type.rimsART-
dc.citation.volume59-
dc.citation.issue17-
dc.citation.beginningpage6894-
dc.citation.endingpage6901-
dc.citation.publicationnameANGEWANDTE CHEMIE-INTERNATIONAL EDITION-
dc.identifier.doi10.1002/anie.201916613-
dc.contributor.localauthorLee, Hee-Yoon-
dc.contributor.localauthorHan, Sunkyu-
dc.contributor.nonIdAuthorKim, Dongwook-
dc.description.isOpenAccessN-
dc.type.journalArticleArticle-
dc.subject.keywordAuthoralkaloids-
dc.subject.keywordAuthorbiomimetic synthesis-
dc.subject.keywordAuthorcyclization-
dc.subject.keywordAuthorrearrangements-
dc.subject.keywordAuthortotal synthesis-
dc.subject.keywordPlusSECUAMAMINE-A-
dc.subject.keywordPlusOXIDATION-
dc.subject.keywordPlusALLOSECURININE-
dc.subject.keywordPlusREARRANGEMENT-
dc.subject.keywordPlusALKALOIDS-
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