Total Synthesis and Configurational Validation of (+)-Violapyrone C
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 | 2021-06-22T23:04:13Z | - |
dc.date.available | 2021-06-22T23:04:13Z | - |
dc.date.created | 2021-01-21 | - |
dc.date.issued | 2014-07 | - |
dc.identifier.issn | 1434-193X | - |
dc.identifier.uri | https://scholarworks.bwise.kr/erica/handle/2021.sw.erica/22424 | - |
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.language | 영어 | - |
dc.language.iso | en | - |
dc.publisher | John Wiley & Sons Ltd. | - |
dc.title | Total Synthesis and Configurational Validation of (+)-Violapyrone C | - |
dc.type | Article | - |
dc.contributor.affiliatedAuthor | Won, Hoshik | - |
dc.identifier.doi | 10.1002/ejoc.201402524 | - |
dc.identifier.scopusid | 2-s2.0-84904502255 | - |
dc.identifier.wosid | 000339493400006 | - |
dc.identifier.bibliographicCitation | European Journal of Organic Chemistry, v.2014, no.21, pp.4472 - 4476 | - |
dc.relation.isPartOf | European Journal of Organic Chemistry | - |
dc.citation.title | European Journal of Organic Chemistry | - |
dc.citation.volume | 2014 | - |
dc.citation.number | 21 | - |
dc.citation.startPage | 4472 | - |
dc.citation.endPage | 4476 | - |
dc.type.rims | ART | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.description.isOpenAccess | N | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Organic | - |
dc.subject.keywordPlus | 3-SUBSTITUTED ISOCOUMARINS | - |
dc.subject.keywordPlus | HETEROCYCLES | - |
dc.subject.keywordPlus | DERIVATIVES | - |
dc.subject.keywordPlus | CYCLIZATION | - |
dc.subject.keywordPlus | ACTIVATION | - |
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.identifier.url | https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201402524 | - |
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