DC Field | Value | Language |
---|---|---|
dc.contributor.author | Kang, Gyumin | ko |
dc.contributor.author | Han, Sunkyu | ko |
dc.date.accessioned | 2022-05-27T03:00:11Z | - |
dc.date.available | 2022-05-27T03:00:11Z | - |
dc.date.created | 2022-05-27 | - |
dc.date.created | 2022-05-27 | - |
dc.date.created | 2022-05-27 | - |
dc.date.issued | 2022-05 | - |
dc.identifier.citation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.144, no.20, pp.8932 - 8937 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10203/296687 | - |
dc.description.abstract | We 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.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.title | Synthesis of Dimeric Securinega Alkaloid Flueggeacosine B: From Pd-Catalyzed Cross-Coupling to Cu-Catalyzed Cross-Dehydrogenative Coupling | - |
dc.type | Article | - |
dc.identifier.wosid | 000805981500010 | - |
dc.identifier.scopusid | 2-s2.0-85131018441 | - |
dc.type.rims | ART | - |
dc.citation.volume | 144 | - |
dc.citation.issue | 20 | - |
dc.citation.beginningpage | 8932 | - |
dc.citation.endingpage | 8937 | - |
dc.citation.publicationname | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.identifier.doi | 10.1021/jacs.2c03861 | - |
dc.contributor.localauthor | Han, Sunkyu | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | TRANSFER RADICAL-ADDITION | - |
dc.subject.keywordPlus | CHEMISTRY | - |
dc.subject.keywordPlus | PHOTOOXYGENATION | - |
dc.subject.keywordPlus | ENAMINES | - |
dc.subject.keywordPlus | ECONOMY | - |
dc.subject.keywordPlus | OLEFINS | - |
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