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Total syntheses of (+/-)-crinine, (+/-)-crinamine, and (+/-)-6a-epi-crinamine via the regioselective synthesis and Diels-Alder reaction of 3-aryl-5-bromo-2-pyrone

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dc.contributor.authorTam, Nguyen Thanh-
dc.contributor.authorChang, Jayhyok-
dc.contributor.authorJung, Eun-Ju-
dc.contributor.authorCho, Cheon-Gyu-
dc.date.accessioned2022-12-21T01:49:17Z-
dc.date.available2022-12-21T01:49:17Z-
dc.date.issued2008-08-
dc.identifier.issn0022-3263-
dc.identifier.issn1520-6904-
dc.identifier.urihttps://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/178109-
dc.description.abstract[GRAPHICS] We have devised a new unified synthetic protocol to (+/-)-crinine, (+/-)-crinamine, and (+/-)-6a-epi-crinamine from the Diels-Alder cycloadduct of 3-(3,4-methylenedioxyphenyl)-5-bromo-2-pyrone with TBS vinyl ether. The requisite 3-(3,4-methylenedioxyphenyl)-5-bromo-2-pyrone was prepared from the C3-selective Stille coupling reaction of 3,5-dibromo-2-pyrone. Also noted is that the vinyl bromide can be used as a handle for further derivatization.-
dc.format.extent7-
dc.language영어-
dc.language.isoENG-
dc.publisherAmerican Chemical Society-
dc.titleTotal syntheses of (+/-)-crinine, (+/-)-crinamine, and (+/-)-6a-epi-crinamine via the regioselective synthesis and Diels-Alder reaction of 3-aryl-5-bromo-2-pyrone-
dc.typeArticle-
dc.publisher.location미국-
dc.identifier.doi10.1021/jo8008353-
dc.identifier.scopusid2-s2.0-50149083686-
dc.identifier.wosid000258332500027-
dc.identifier.bibliographicCitationThe Journal of Organic Chemistry, v.73, no.16, pp 6258 - 6264-
dc.citation.titleThe Journal of Organic Chemistry-
dc.citation.volume73-
dc.citation.number16-
dc.citation.startPage6258-
dc.citation.endPage6264-
dc.type.docTypeArticle-
dc.description.isOpenAccessN-
dc.description.journalRegisteredClassscie-
dc.description.journalRegisteredClassscopus-
dc.relation.journalResearchAreaChemistry-
dc.relation.journalWebOfScienceCategoryChemistry, Organic-
dc.subject.keywordPlusAZA-COPE REARRANGEMENTS-
dc.subject.keywordPlusAMARYLLIDACEAE ALKALOIDS-
dc.subject.keywordPlusCYCLOADDITIONS-
dc.subject.keywordPlusTANDEM-
dc.subject.keywordPlusCIS-3A-ARYLOCTAHYDROINDOLES-
dc.subject.keywordPlus3,5-DIBROMO-2-PYRONE-
dc.subject.keywordPlus(-)-HAEMANTHIDINE-
dc.subject.keywordPlus(-)-AMABILINE-
dc.subject.keywordPlusCRININE-
dc.subject.keywordPlusROUTE-
dc.identifier.urlhttps://pubs.acs.org/doi/10.1021/jo8008353-
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