Total Synthesis and Configurational Validation of (+)-Violapyrone C SCIE SCOPUS

DC Field Value Language
dc.contributor.author Lee, Jong Seok -
dc.contributor.author Shin, Junho -
dc.contributor.author Shin, Hee Jae -
dc.contributor.author Lee, Hwa-Sun -
dc.contributor.author Lee, Yeon-Ju -
dc.contributor.author Lee, Hyi-Seung -
dc.contributor.author Won, Hoshik -
dc.date.accessioned 2020-04-20T04:40:24Z -
dc.date.available 2020-04-20T04:40:24Z -
dc.date.created 2020-01-28 -
dc.date.issued 2014-07 -
dc.identifier.issn 1434-193X -
dc.identifier.uri https://sciwatch.kiost.ac.kr/handle/2020.kiost/2780 -
dc.description.abstract Gold(I)-catalyzed intramolecular 6-endo-dig cyclization of tert-butyl ynoates afforded alpha-pyrone cores of violapyrones. Moreover, this reaction was successfully applied to the stereospecific syntheses of (+)- and (-)-violapyrone C, which allowed the absolute configuration of natural (+)-violapyrone C to be assigned by comparison of the optical rotations. This first total synthesis, which proceeded in 22% yield over 10 steps from (S)-(-)-2-methylbutanol, features silver(I) oxide promoted monobenzylation of 1,4-butanediol, Wittig ole-fination, Claisen condensation, Corey-Fuchs reaction, and gold(I)-catalyzed alpha-pyrone synthesis. -
dc.description.uri 1 -
dc.language English -
dc.publisher WILEY-V C H VERLAG GMBH -
dc.subject 1ST TOTAL-SYNTHESIS -
dc.subject REGIOSELECTIVE SYNTHESIS -
dc.subject 3-SUBSTITUTED ISOCOUMARINS -
dc.subject COUPLING REACTIONS -
dc.subject GOLD -
dc.subject DERIVATIVES -
dc.subject ACIDS -
dc.subject CYCLIZATION -
dc.subject HETEROCYCLES -
dc.subject SUBSTITUENT -
dc.title Total Synthesis and Configurational Validation of (+)-Violapyrone C -
dc.type Article -
dc.citation.endPage 4476 -
dc.citation.startPage 4472 -
dc.citation.title EUROPEAN JOURNAL OF ORGANIC CHEMISTRY -
dc.citation.number 21 -
dc.contributor.alternativeName 이종석 -
dc.contributor.alternativeName 신준호 -
dc.contributor.alternativeName 신희재 -
dc.contributor.alternativeName 이화선 -
dc.contributor.alternativeName 이연주 -
dc.contributor.alternativeName 이희승 -
dc.identifier.bibliographicCitation EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, no.21, pp.4472 - 4476 -
dc.identifier.doi 10.1002/ejoc.201402524 -
dc.identifier.scopusid 2-s2.0-84904502255 -
dc.identifier.wosid 000339493400006 -
dc.type.docType Article -
dc.description.journalClass 1 -
dc.subject.keywordPlus 1ST TOTAL-SYNTHESIS -
dc.subject.keywordPlus REGIOSELECTIVE SYNTHESIS -
dc.subject.keywordPlus 3-SUBSTITUTED ISOCOUMARINS -
dc.subject.keywordPlus COUPLING REACTIONS -
dc.subject.keywordPlus GOLD -
dc.subject.keywordPlus DERIVATIVES -
dc.subject.keywordPlus ACIDS -
dc.subject.keywordPlus CYCLIZATION -
dc.subject.keywordPlus HETEROCYCLES -
dc.subject.keywordPlus SUBSTITUENT -
dc.subject.keywordAuthor Total synthesis -
dc.subject.keywordAuthor Natural products -
dc.subject.keywordAuthor Oxygen heterocycles -
dc.subject.keywordAuthor Gold -
dc.subject.keywordAuthor Wittig reactions -
dc.relation.journalWebOfScienceCategory Chemistry, Organic -
dc.description.journalRegisteredClass scie -
dc.description.journalRegisteredClass scopus -
dc.relation.journalResearchArea Chemistry -
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Marine Resources Research Division > Marine Biotechnology Research Center > 1. Journal Articles
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