DC Field | Value | Language |
---|---|---|
dc.contributor.author | Lee, Sanghyeon | ko |
dc.contributor.author | Kang, Gyumin | ko |
dc.contributor.author | Chung, Garam | ko |
dc.contributor.author | Kim, Dongwook | ko |
dc.contributor.author | Lee, Hee-Yoon | ko |
dc.contributor.author | Han, Sunkyu | ko |
dc.date.accessioned | 2020-04-14T07:20:15Z | - |
dc.date.available | 2020-04-14T07:20:15Z | - |
dc.date.created | 2020-04-14 | - |
dc.date.created | 2020-04-14 | - |
dc.date.created | 2020-04-14 | - |
dc.date.created | 2020-04-14 | - |
dc.date.issued | 2020-04 | - |
dc.identifier.citation | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.59, no.17, pp.6894 - 6901 | - |
dc.identifier.issn | 1433-7851 | - |
dc.identifier.uri | http://hdl.handle.net/10203/273891 | - |
dc.description.abstract | Presented 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.language | English | - |
dc.publisher | WILEY-V C H VERLAG GMBH | - |
dc.title | Biosynthetically Inspired Syntheses of Secu′amamine A and Fluvirosaones A and B | - |
dc.type | Article | - |
dc.identifier.wosid | 000525279800039 | - |
dc.identifier.scopusid | 2-s2.0-85081257277 | - |
dc.type.rims | ART | - |
dc.citation.volume | 59 | - |
dc.citation.issue | 17 | - |
dc.citation.beginningpage | 6894 | - |
dc.citation.endingpage | 6901 | - |
dc.citation.publicationname | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | - |
dc.identifier.doi | 10.1002/anie.201916613 | - |
dc.contributor.localauthor | Lee, Hee-Yoon | - |
dc.contributor.localauthor | Han, Sunkyu | - |
dc.contributor.nonIdAuthor | Kim, Dongwook | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordAuthor | alkaloids | - |
dc.subject.keywordAuthor | biomimetic synthesis | - |
dc.subject.keywordAuthor | cyclization | - |
dc.subject.keywordAuthor | rearrangements | - |
dc.subject.keywordAuthor | total synthesis | - |
dc.subject.keywordPlus | SECUAMAMINE-A | - |
dc.subject.keywordPlus | OXIDATION | - |
dc.subject.keywordPlus | ALLOSECURININE | - |
dc.subject.keywordPlus | REARRANGEMENT | - |
dc.subject.keywordPlus | ALKALOIDS | - |
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