Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach
DC Field | Value | Language |
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dc.contributor.author | Yoon, Hojong | - |
dc.contributor.author | Cho, Kyung Seon | - |
dc.contributor.author | Sim, Taebo | - |
dc.date.accessioned | 2021-09-05T09:31:57Z | - |
dc.date.available | 2021-09-05T09:31:57Z | - |
dc.date.created | 2021-06-15 | - |
dc.date.issued | 2014-04-15 | - |
dc.identifier.issn | 0957-4166 | - |
dc.identifier.uri | https://scholar.korea.ac.kr/handle/2021.sw.korea/98759 | - |
dc.description.abstract | The synthesis of the indolizidine alkaloid, (+)-lentiginosine, is described. A key feature of the preparative route is the efficient and stereoselective construction of a dihydroxylated pyrrolidine via Sharpless asymmetric dihydroxylation of an aziridine-enoate, which was prepared from commercially available 1-(S)-alpha-methylbenzylaziridine-2-methanol. In addition, a regioselective aziridine-to-pyrrolidinone ring expansion process followed by a Wittig olefination was employed to construct a late stage pyrrolidine intermediate that was transformed into (+)-lentiginosine. (c) 2014 Elsevier Ltd. All rights reserved. | - |
dc.language | English | - |
dc.language.iso | en | - |
dc.publisher | PERGAMON-ELSEVIER SCIENCE LTD | - |
dc.subject | CONCISE TOTAL-SYNTHESIS | - |
dc.subject | DIRECTED DIHYDROXYLATION | - |
dc.subject | STEREOSELECTIVE-SYNTHESIS | - |
dc.subject | ALLYLIC ALCOHOLS | - |
dc.subject | POLYHYDROXYLATED ALKALOIDS | - |
dc.subject | ABSOLUTE-CONFIGURATION | - |
dc.subject | LENTIGINOSINE | - |
dc.subject | INHIBITORS | - |
dc.subject | TRICHLOROACETAMIDES | - |
dc.subject | (-)-LENTIGINOSINE | - |
dc.title | Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach | - |
dc.type | Article | - |
dc.contributor.affiliatedAuthor | Sim, Taebo | - |
dc.identifier.doi | 10.1016/j.tetasy.2014.02.009 | - |
dc.identifier.wosid | 000335628100004 | - |
dc.identifier.bibliographicCitation | TETRAHEDRON-ASYMMETRY, v.25, no.6-7, pp.497 - 502 | - |
dc.relation.isPartOf | TETRAHEDRON-ASYMMETRY | - |
dc.citation.title | TETRAHEDRON-ASYMMETRY | - |
dc.citation.volume | 25 | - |
dc.citation.number | 6-7 | - |
dc.citation.startPage | 497 | - |
dc.citation.endPage | 502 | - |
dc.type.rims | ART | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Inorganic & Nuclear | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Organic | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Physical | - |
dc.subject.keywordPlus | CONCISE TOTAL-SYNTHESIS | - |
dc.subject.keywordPlus | DIRECTED DIHYDROXYLATION | - |
dc.subject.keywordPlus | STEREOSELECTIVE-SYNTHESIS | - |
dc.subject.keywordPlus | ALLYLIC ALCOHOLS | - |
dc.subject.keywordPlus | POLYHYDROXYLATED ALKALOIDS | - |
dc.subject.keywordPlus | ABSOLUTE-CONFIGURATION | - |
dc.subject.keywordPlus | LENTIGINOSINE | - |
dc.subject.keywordPlus | INHIBITORS | - |
dc.subject.keywordPlus | TRICHLOROACETAMIDES | - |
dc.subject.keywordPlus | (-)-LENTIGINOSINE | - |
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