Oxetane cis- and trans-beta-amino-acid scaffolds from L-rhamnose by efficient S(N)2 reactions in oxetane rings; pseudoenantiomeric analogues of the antibiotic oxetin
An efficient multigram ring contraction of a 1,4-lactone 2-O-triflate derived from l-rhamnose - with retention of configuration in the ring closure - is the key step in the preparation of a series of oxetanes, which are pseudoenantiomeric analogues of the naturally occurring antibiotic oxetin, an ox...
| Glavni autori: | , , , , , |
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| Format: | Journal article |
| Jezik: | English |
| Izdano: |
2004
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| _version_ | 1826287851760779264 |
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| author | Johnson, S Jenkinson, S Angus, D Jones, J Fleet, G Taillefumier, C |
| author_facet | Johnson, S Jenkinson, S Angus, D Jones, J Fleet, G Taillefumier, C |
| author_sort | Johnson, S |
| collection | OXFORD |
| description | An efficient multigram ring contraction of a 1,4-lactone 2-O-triflate derived from l-rhamnose - with retention of configuration in the ring closure - is the key step in the preparation of a series of oxetanes, which are pseudoenantiomeric analogues of the naturally occurring antibiotic oxetin, an oxetane cis-β-amino acid. Subsequent nucleophilic displacements of the corresponding triflates by azide proceed in consistently excellent yields, without any elimination, to provide syntheses of scaffolds for analogues of the antibiotic. © 2004 Elsevier Ltd. All rights reserved. |
| first_indexed | 2024-03-07T02:04:52Z |
| format | Journal article |
| id | oxford-uuid:9ea376cb-a1bf-4281-9b9c-7f490699f14a |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T02:04:52Z |
| publishDate | 2004 |
| record_format | dspace |
| spelling | oxford-uuid:9ea376cb-a1bf-4281-9b9c-7f490699f14a2022-03-27T00:51:24ZOxetane cis- and trans-beta-amino-acid scaffolds from L-rhamnose by efficient S(N)2 reactions in oxetane rings; pseudoenantiomeric analogues of the antibiotic oxetinJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:9ea376cb-a1bf-4281-9b9c-7f490699f14aEnglishSymplectic Elements at Oxford2004Johnson, SJenkinson, SAngus, DJones, JFleet, GTaillefumier, CAn efficient multigram ring contraction of a 1,4-lactone 2-O-triflate derived from l-rhamnose - with retention of configuration in the ring closure - is the key step in the preparation of a series of oxetanes, which are pseudoenantiomeric analogues of the naturally occurring antibiotic oxetin, an oxetane cis-β-amino acid. Subsequent nucleophilic displacements of the corresponding triflates by azide proceed in consistently excellent yields, without any elimination, to provide syntheses of scaffolds for analogues of the antibiotic. © 2004 Elsevier Ltd. All rights reserved. |
| spellingShingle | Johnson, S Jenkinson, S Angus, D Jones, J Fleet, G Taillefumier, C Oxetane cis- and trans-beta-amino-acid scaffolds from L-rhamnose by efficient S(N)2 reactions in oxetane rings; pseudoenantiomeric analogues of the antibiotic oxetin |
| title | Oxetane cis- and trans-beta-amino-acid scaffolds from L-rhamnose by efficient S(N)2 reactions in oxetane rings; pseudoenantiomeric analogues of the antibiotic oxetin |
| title_full | Oxetane cis- and trans-beta-amino-acid scaffolds from L-rhamnose by efficient S(N)2 reactions in oxetane rings; pseudoenantiomeric analogues of the antibiotic oxetin |
| title_fullStr | Oxetane cis- and trans-beta-amino-acid scaffolds from L-rhamnose by efficient S(N)2 reactions in oxetane rings; pseudoenantiomeric analogues of the antibiotic oxetin |
| title_full_unstemmed | Oxetane cis- and trans-beta-amino-acid scaffolds from L-rhamnose by efficient S(N)2 reactions in oxetane rings; pseudoenantiomeric analogues of the antibiotic oxetin |
| title_short | Oxetane cis- and trans-beta-amino-acid scaffolds from L-rhamnose by efficient S(N)2 reactions in oxetane rings; pseudoenantiomeric analogues of the antibiotic oxetin |
| title_sort | oxetane cis and trans beta amino acid scaffolds from l rhamnose by efficient s n 2 reactions in oxetane rings pseudoenantiomeric analogues of the antibiotic oxetin |
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