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dc.contributor.authorSengupta, Sandip-
dc.contributor.authorKim, Hak Joong-
dc.contributor.authorCho, Kyung Seon-
dc.contributor.authorSong, Woon Young-
dc.contributor.authorSim, Taebo-
dc.date.accessioned2024-01-20T02:03:20Z-
dc.date.available2024-01-20T02:03:20Z-
dc.date.created2022-01-10-
dc.date.issued2017-02-23-
dc.identifier.issn0040-4020-
dc.identifier.urihttps://pubs.kist.re.kr/handle/201004/123048-
dc.description.abstractA highly diastereoselective and efficient convergent synthesis of mupirocin H starting from (+)-(R)-Roche ester was achieved. Grubbs cross metathesis was employed as the key step in the pathway to generate an important E-olefin intermediate. Other processes utilized in the route include a Pd-catalysed stereoselective substitution reaction of a cis epoxide, Sharpless epoxidation followed by Red-Al promoted epoxide ring opening, and Seebach methylation and a TEMPO/BAIB mediated oxidation-lactonization sequence. Finally, we observed that mupirocin H inhibits SbnE, a synthetase required for staphyloferrin B biosynthesis. (C)2017 Elsevier Ltd. All rights reserved.-
dc.languageEnglish-
dc.publisherPERGAMON-ELSEVIER SCIENCE LTD-
dc.subjectOLEFIN CROSS-METATHESIS-
dc.subjectENANTIOSELECTIVE SYNTHESIS-
dc.subjectGENE-CLUSTER-
dc.subjectPSEUDOMONAS-FLUORESCENS-
dc.subjectDIMETHYL-SULFOXIDE-
dc.subjectCARBONYL-COMPOUNDS-
dc.subjectOXALYL CHLORIDE-
dc.subjectMALIC-ACID-
dc.subjectOXIDATION-
dc.subjectALCOHOLS-
dc.titleHighly stereoselective synthesis of mupirocin H-
dc.typeArticle-
dc.identifier.doi10.1016/j.tet.2017.01.017-
dc.description.journalClass1-
dc.identifier.bibliographicCitationTETRAHEDRON, v.73, no.8, pp.1182 - 1189-
dc.citation.titleTETRAHEDRON-
dc.citation.volume73-
dc.citation.number8-
dc.citation.startPage1182-
dc.citation.endPage1189-
dc.description.journalRegisteredClassscie-
dc.description.journalRegisteredClassscopus-
dc.identifier.wosid000394194400014-
dc.identifier.scopusid2-s2.0-85009739536-
dc.relation.journalWebOfScienceCategoryChemistry, Organic-
dc.relation.journalResearchAreaChemistry-
dc.type.docTypeArticle-
dc.subject.keywordPlusOLEFIN CROSS-METATHESIS-
dc.subject.keywordPlusENANTIOSELECTIVE SYNTHESIS-
dc.subject.keywordPlusGENE-CLUSTER-
dc.subject.keywordPlusPSEUDOMONAS-FLUORESCENS-
dc.subject.keywordPlusDIMETHYL-SULFOXIDE-
dc.subject.keywordPlusCARBONYL-COMPOUNDS-
dc.subject.keywordPlusOXALYL CHLORIDE-
dc.subject.keywordPlusMALIC-ACID-
dc.subject.keywordPlusOXIDATION-
dc.subject.keywordPlusALCOHOLS-
dc.subject.keywordAuthorMupirocin H-
dc.subject.keywordAuthorTotal synthesis-
dc.subject.keywordAuthor(+)-(R)-Roche ester-
dc.subject.keywordAuthorGrubbs cross metathesis-
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