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분자활성촉매반응연구단
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Diastereoselective Rhodium-Catalyzed [(3+2+2)] Carbocyclization Reactions with Tethered Alkynylidenecyclopropanes: Synthesis of the Tremulane Sesquiterpene Natural Products

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dc.contributor.authorEvans, P. Andrew-
dc.contributor.authorDushnicky, Molly J.-
dc.contributor.authorDasol Cho-
dc.contributor.authorMajhi, Jadab-
dc.contributor.authorSeulhui Choi-
dc.contributor.authorPipaliya, Bhavin V.-
dc.contributor.authorInglesby, Phillip A.-
dc.contributor.authorMu-Hyun Baik-
dc.date.accessioned2021-08-27T05:50:06Z-
dc.date.accessioned2021-08-27T05:50:07Z-
dc.date.available2021-08-27T05:50:06Z-
dc.date.available2021-08-27T05:50:07Z-
dc.date.created2021-03-11-
dc.date.issued2021-08-
dc.identifier.issn2193-5807-
dc.identifier.urihttps://pr.ibs.re.kr/handle/8788114/10165-
dc.description.abstractThe development of a diastereoselective intramolecular rhodium-catalyzed [(3+2+2)] carbocyclization reactions of allyl ester-tethered alkynylidenecyclopropanes (ACPs) for the construction of the 5,7,5-tricyclic scaffold of the tremulane sesquiterpene natural products is described. This work illustrates that the stereoelectronic nature of the phosphite ligand is critical for attaining high levels of stereocontrol, which is supported by density functional theory (DFT) studies that indicate the migratory insertion step favors the formation of the cis-diastereoisomer. Consequently, several strategies were devised to access the thermodynamically more stable trans-diastereoisomer for the synthesis of the tremulanes; however, the attempts to either switch the sense of stereocontrol in the carbocyclization reaction or epimerize the C7 stereocenter of the cycloadduct provided only modest improvements. Hence, we elected to highlight the synthetic utility of this strategy with the development of concise and highly efficient syntheses of (+/-)-epi-tremulenolide A, (+/-)-epi-tremulenediol A and (+/-)-epi-ceriponol D.-
dc.language영어-
dc.publisherWILEY-V C H VERLAG GMBH-
dc.titleDiastereoselective Rhodium-Catalyzed [(3+2+2)] Carbocyclization Reactions with Tethered Alkynylidenecyclopropanes: Synthesis of the Tremulane Sesquiterpene Natural Products-
dc.typeArticle-
dc.type.rimsART-
dc.identifier.wosid000620686400001-
dc.identifier.scopusid2-s2.0-85101287020-
dc.identifier.rimsid75034-
dc.contributor.affiliatedAuthorDasol Cho-
dc.contributor.affiliatedAuthorSeulhui Choi-
dc.contributor.affiliatedAuthorMu-Hyun Baik-
dc.identifier.doi10.1002/ajoc.202000482-
dc.identifier.bibliographicCitationASIAN JOURNAL OF ORGANIC CHEMISTRY, v.10, no.8, pp.2174 - 2183-
dc.relation.isPartOfASIAN JOURNAL OF ORGANIC CHEMISTRY-
dc.citation.titleASIAN JOURNAL OF ORGANIC CHEMISTRY-
dc.citation.volume10-
dc.citation.number8-
dc.citation.startPage2174-
dc.citation.endPage2183-
dc.type.docTypeArticle-
dc.description.journalClass1-
dc.description.journalClass1-
dc.description.isOpenAccessN-
dc.description.journalRegisteredClassscie-
dc.description.journalRegisteredClassscopus-
dc.relation.journalResearchAreaChemistry-
dc.relation.journalWebOfScienceCategoryChemistry, Organic-
dc.subject.keywordAuthorcyclizations-
dc.subject.keywordAuthornatural products-
dc.subject.keywordAuthorrhodium-catalyzed-
dc.subject.keywordAuthorstereocontrol-
dc.subject.keywordAuthorsynthetic methods-
dc.subject.keywordAuthortremulanes-
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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