Stereoselective Synthesis of (+)-Polyoxamic Acid Starting with a Chiral Aziridine
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Yoon, Hojong | - |
dc.contributor.author | Sim, Taebo | - |
dc.date.accessioned | 2021-09-05T18:04:15Z | - |
dc.date.available | 2021-09-05T18:04:15Z | - |
dc.date.created | 2021-06-15 | - |
dc.date.issued | 2013-12-02 | - |
dc.identifier.issn | 0039-7881 | - |
dc.identifier.uri | https://scholar.korea.ac.kr/handle/2021.sw.korea/101319 | - |
dc.description.abstract | An efficient and stereoselective synthesis of (+)-polyoxamic acid was developed. The route starts with the commercially available 1-(R)--methylbenzylaziridine-2-methanol, a substance that has not been used previously as a starting material for the preparation of this target. The route also features the use of a stereocontrolled Sharpless asymmetric dihydroxylation reaction, promoted by AD-mix-, which is followed by a regioselective aziridine ring-opening process, to generate the basic skeleton of target natural product. Subsequent oxidation and global deprotection produces (+)-polyoxamic acid. | - |
dc.language | English | - |
dc.language.iso | en | - |
dc.publisher | GEORG THIEME VERLAG KG | - |
dc.subject | ALPHA-AMINO-ACIDS | - |
dc.subject | POLYOXAMIC ACID | - |
dc.subject | ASYMMETRIC-SYNTHESIS | - |
dc.subject | EFFICIENT SYNTHESIS | - |
dc.subject | REARRANGEMENT | - |
dc.subject | ANTIBIOTICS | - |
dc.subject | DERIVATIVES | - |
dc.subject | POLYOXINS | - |
dc.title | Stereoselective Synthesis of (+)-Polyoxamic Acid Starting with a Chiral Aziridine | - |
dc.type | Article | - |
dc.contributor.affiliatedAuthor | Sim, Taebo | - |
dc.identifier.doi | 10.1055/s-0033-1338545 | - |
dc.identifier.wosid | 000327193900014 | - |
dc.identifier.bibliographicCitation | SYNTHESIS-STUTTGART, v.45, no.23, pp.3276 - 3280 | - |
dc.relation.isPartOf | SYNTHESIS-STUTTGART | - |
dc.citation.title | SYNTHESIS-STUTTGART | - |
dc.citation.volume | 45 | - |
dc.citation.number | 23 | - |
dc.citation.startPage | 3276 | - |
dc.citation.endPage | 3280 | - |
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, Organic | - |
dc.subject.keywordPlus | ALPHA-AMINO-ACIDS | - |
dc.subject.keywordPlus | POLYOXAMIC ACID | - |
dc.subject.keywordPlus | ASYMMETRIC-SYNTHESIS | - |
dc.subject.keywordPlus | EFFICIENT SYNTHESIS | - |
dc.subject.keywordPlus | REARRANGEMENT | - |
dc.subject.keywordPlus | ANTIBIOTICS | - |
dc.subject.keywordPlus | DERIVATIVES | - |
dc.subject.keywordPlus | POLYOXINS | - |
dc.subject.keywordAuthor | polyhydroxylated amino acid | - |
dc.subject.keywordAuthor | (+)-polyoxamic acid | - |
dc.subject.keywordAuthor | natural product synthesis | - |
dc.subject.keywordAuthor | chiral aziridine | - |
dc.subject.keywordAuthor | asymmetric dihydroxylation | - |
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