Synthesis of Dimeric Securinega Alkaloid Flueggeacosine B: From Pd-Catalyzed Cross-Coupling to Cu-Catalyzed Cross-Dehydrogenative Coupling

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dc.contributor.authorKang, Gyuminko
dc.contributor.authorHan, Sunkyuko
dc.date.accessioned2022-05-27T03:00:11Z-
dc.date.available2022-05-27T03:00:11Z-
dc.date.created2022-05-27-
dc.date.created2022-05-27-
dc.date.created2022-05-27-
dc.date.issued2022-05-
dc.identifier.citationJOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.144, no.20, pp.8932 - 8937-
dc.identifier.issn0002-7863-
dc.identifier.urihttp://hdl.handle.net/10203/296687-
dc.description.abstractWe completed the synthesis of dimeric high-oxidation-state securinega alkaloid flueggeacosine B via two synthetic routes from allosecurinine. The first-generation synthesis (seven overall steps) involved a Liebeskind–Srogl cross-coupling reaction for the union of two functionalized fragments, the organostannane and the thioester. As a means to further streamline the synthetic route, we have developed a visible-light-mediated Cu-catalyzed cross-dehydrogenative coupling (CDC) reaction between an aldehyde and an electron-deficient olefin. This enabled the second-generation synthesis of flueggeacosine B from allosecurinine in four overall steps. The newly developed CDC reaction paves a direct way to a conjugated dicarbonyl moiety, a ubiquitous structural moiety present in various natural products.-
dc.languageEnglish-
dc.publisherAMER CHEMICAL SOC-
dc.titleSynthesis of Dimeric Securinega Alkaloid Flueggeacosine B: From Pd-Catalyzed Cross-Coupling to Cu-Catalyzed Cross-Dehydrogenative Coupling-
dc.typeArticle-
dc.identifier.wosid000805981500010-
dc.identifier.scopusid2-s2.0-85131018441-
dc.type.rimsART-
dc.citation.volume144-
dc.citation.issue20-
dc.citation.beginningpage8932-
dc.citation.endingpage8937-
dc.citation.publicationnameJOURNAL OF THE AMERICAN CHEMICAL SOCIETY-
dc.identifier.doi10.1021/jacs.2c03861-
dc.contributor.localauthorHan, Sunkyu-
dc.description.isOpenAccessN-
dc.type.journalArticleArticle-
dc.subject.keywordPlusTRANSFER RADICAL-ADDITION-
dc.subject.keywordPlusCHEMISTRY-
dc.subject.keywordPlusPHOTOOXYGENATION-
dc.subject.keywordPlusENAMINES-
dc.subject.keywordPlusECONOMY-
dc.subject.keywordPlusOLEFINS-
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