Dimerization Strategies for the Synthesis of High-Order Securinega Alkaloids
DC Field | Value | Language |
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dc.contributor.author | Joonoh Park | - |
dc.contributor.author | Seongmin Jeon | - |
dc.contributor.author | Gyumin Kang | - |
dc.contributor.author | Jongsun Lee | - |
dc.contributor.author | Mu-Hyun Baik | - |
dc.contributor.author | Sunkyu Han | - |
dc.date.available | 2019-05-02T08:08:48Z | - |
dc.date.created | 2019-02-18 | - |
dc.date.issued | 2019-02 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | https://pr.ibs.re.kr/handle/8788114/5705 | - |
dc.description.abstract | We describe different modes of dimerization of various α′,γ-dioxyenone derivatives with potential applications to the synthesis of high-order securinega alkaloids. We learned that the relative stereochemical relationship between α′- and γ-hydroxyl groups of the α′,γ-dihydroxyenone derivative determines the mode of dimerization. While cis-α′,γ-dioxyenone 26 provided the Rauhut-Currier-type (RC-type) dimer 31 upon reaction with TBAF, trans-α′,γ-dihydroxyenone 34 afforded dimeric tetrahydrofuran derivative 41 under the same reaction conditions. We also noticed that the protection of the γ-hydroxyl group drastically changes the reaction outcomes. While cis-α′-oxy-γ-OPiv-enone 49 did not show any reactivity in the presence of TBAF, trans-α′-hydroxy-γ-OPiv-enone 45 produced the RC-type dimer 46 under the same reaction conditions. Computational analysis revealed the detailed mechanism of the latter transformation. Copyright © 2018 American Chemical Society. | - |
dc.description.uri | 1 | - |
dc.language | 영어 | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.title | Dimerization Strategies for the Synthesis of High-Order Securinega Alkaloids | - |
dc.type | Article | - |
dc.type.rims | ART | - |
dc.identifier.wosid | 000457947800027 | - |
dc.identifier.scopusid | 2-s2.0-85060063879 | - |
dc.identifier.rimsid | 67027 | - |
dc.contributor.affiliatedAuthor | Joonoh Park | - |
dc.contributor.affiliatedAuthor | Gyumin Kang | - |
dc.contributor.affiliatedAuthor | Jongsun Lee | - |
dc.contributor.affiliatedAuthor | Mu-Hyun Baik | - |
dc.contributor.affiliatedAuthor | Sunkyu Han | - |
dc.identifier.doi | 10.1021/acs.joc.8b02852 | - |
dc.identifier.bibliographicCitation | JOURNAL OF ORGANIC CHEMISTRY, v.84, no.3, pp.1398 - 1406 | - |
dc.citation.title | JOURNAL OF ORGANIC CHEMISTRY | - |
dc.citation.volume | 84 | - |
dc.citation.number | 3 | - |
dc.citation.startPage | 1398 | - |
dc.citation.endPage | 1406 | - |
dc.description.journalClass | 1 | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |