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dc.contributor.authorLee, Baeck Kyoung-
dc.contributor.authorChoi, Hwan Geun-
dc.contributor.authorRoh, Eun Joo-
dc.contributor.authorLee, Won Koo-
dc.contributor.authorSim, Taebo-
dc.date.accessioned2024-01-20T13:01:49Z-
dc.date.available2024-01-20T13:01:49Z-
dc.date.created2021-09-01-
dc.date.issued2013-02-06-
dc.identifier.issn0040-4039-
dc.identifier.urihttps://pubs.kist.re.kr/handle/201004/128361-
dc.description.abstractAn efficient synthesis of (-)-8-epi-swainsonine, starting from a commercially available 1-(R)-alpha-methylbenzylaziridine-2-methanol, was developed. The synthetic route utilizes stereocontrolled Sharpless asymmetric dihydroxylation governed by AD-mix-beta followed by an aziridine ring opening-cyclization sequence to generate the five membered N-heterocyclic ring system present in the bicyclic target. A subsequent stereoselective allylation and piperidine ring forming cyclization then produced a precursor that was converted into (-)-8-epi-swainsonine. (c) 2012 Elsevier Ltd. All rights reserved.-
dc.languageEnglish-
dc.publisherPERGAMON-ELSEVIER SCIENCE LTD-
dc.subjectRING-CLOSING METATHESIS-
dc.subjectASYMMETRIC SYNTHESES-
dc.subjectSWAINSONA-CANESCENS-
dc.subjectNATURAL OCCURRENCE-
dc.subjectALPHA-MANNOSIDASE-
dc.subject(-)-SWAINSONINE-
dc.subjectINHIBITION-
dc.subjectALKALOIDS-
dc.subjectANALOGS-
dc.subjectDIHYDROXYLATION-
dc.titleStereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine-
dc.typeArticle-
dc.identifier.doi10.1016/j.tetlet.2012.11.087-
dc.description.journalClass1-
dc.identifier.bibliographicCitationTETRAHEDRON LETTERS, v.54, no.6, pp.553 - 556-
dc.citation.titleTETRAHEDRON LETTERS-
dc.citation.volume54-
dc.citation.number6-
dc.citation.startPage553-
dc.citation.endPage556-
dc.description.journalRegisteredClassscie-
dc.description.journalRegisteredClassscopus-
dc.identifier.wosid000314388300026-
dc.identifier.scopusid2-s2.0-84872018243-
dc.relation.journalWebOfScienceCategoryChemistry, Organic-
dc.relation.journalResearchAreaChemistry-
dc.type.docTypeArticle-
dc.subject.keywordPlusRING-CLOSING METATHESIS-
dc.subject.keywordPlusASYMMETRIC SYNTHESES-
dc.subject.keywordPlusSWAINSONA-CANESCENS-
dc.subject.keywordPlusNATURAL OCCURRENCE-
dc.subject.keywordPlusALPHA-MANNOSIDASE-
dc.subject.keywordPlus(-)-SWAINSONINE-
dc.subject.keywordPlusINHIBITION-
dc.subject.keywordPlusALKALOIDS-
dc.subject.keywordPlusANALOGS-
dc.subject.keywordPlusDIHYDROXYLATION-
dc.subject.keywordAuthorIndolizidine alkaloids-
dc.subject.keywordAuthor(-)-8-Epi-swainsonine-
dc.subject.keywordAuthorTotal synthesis-
dc.subject.keywordAuthorAziridine-
dc.subject.keywordAuthorNatural product-
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