Syntheses of (6S)-cephalosporins from 6-aminopenicillanic acid
Two practical routes to (6S,7S)-cephalosporins from 6-aminopenicillanic acid (6-APA) are described. In the first, 6-APA was converted to (2S,4S,5S,6S)-penicillin sulfoxide 49, which underwent Morin ring expansion to a protected (6S,7S)-cephem 50. In the second, ester 15 was converted to (2S,4S,5S,6R...
| Váldodahkkit: | , , , , , |
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| Materiálatiipa: | Journal article |
| Giella: | English |
| Almmustuhtton: |
2000
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| _version_ | 1826270282462003200 |
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| author | Fekner, T Baldwin, J Adlington, R Jones, T Prout, C Schofield, C |
| author_facet | Fekner, T Baldwin, J Adlington, R Jones, T Prout, C Schofield, C |
| author_sort | Fekner, T |
| collection | OXFORD |
| description | Two practical routes to (6S,7S)-cephalosporins from 6-aminopenicillanic acid (6-APA) are described. In the first, 6-APA was converted to (2S,4S,5S,6S)-penicillin sulfoxide 49, which underwent Morin ring expansion to a protected (6S,7S)-cephem 50. In the second, ester 15 was converted to (2S,4S,5S,6R)-penicillin sulfoxide 58, which was then transformed into (6S,7R)-cephem 59. Different methods for the epimerisation of the C-7 position of cephem 59 were examined. (C) 2000 Elsevier Science Ltd. |
| first_indexed | 2024-03-06T21:38:25Z |
| format | Journal article |
| id | oxford-uuid:470e182e-ff02-48f7-881e-1e548dea86b5 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T21:38:25Z |
| publishDate | 2000 |
| record_format | dspace |
| spelling | oxford-uuid:470e182e-ff02-48f7-881e-1e548dea86b52022-03-26T15:17:45ZSyntheses of (6S)-cephalosporins from 6-aminopenicillanic acidJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:470e182e-ff02-48f7-881e-1e548dea86b5EnglishSymplectic Elements at Oxford2000Fekner, TBaldwin, JAdlington, RJones, TProut, CSchofield, CTwo practical routes to (6S,7S)-cephalosporins from 6-aminopenicillanic acid (6-APA) are described. In the first, 6-APA was converted to (2S,4S,5S,6S)-penicillin sulfoxide 49, which underwent Morin ring expansion to a protected (6S,7S)-cephem 50. In the second, ester 15 was converted to (2S,4S,5S,6R)-penicillin sulfoxide 58, which was then transformed into (6S,7R)-cephem 59. Different methods for the epimerisation of the C-7 position of cephem 59 were examined. (C) 2000 Elsevier Science Ltd. |
| spellingShingle | Fekner, T Baldwin, J Adlington, R Jones, T Prout, C Schofield, C Syntheses of (6S)-cephalosporins from 6-aminopenicillanic acid |
| title | Syntheses of (6S)-cephalosporins from 6-aminopenicillanic acid |
| title_full | Syntheses of (6S)-cephalosporins from 6-aminopenicillanic acid |
| title_fullStr | Syntheses of (6S)-cephalosporins from 6-aminopenicillanic acid |
| title_full_unstemmed | Syntheses of (6S)-cephalosporins from 6-aminopenicillanic acid |
| title_short | Syntheses of (6S)-cephalosporins from 6-aminopenicillanic acid |
| title_sort | syntheses of 6s cephalosporins from 6 aminopenicillanic acid |
| work_keys_str_mv | AT feknert synthesesof6scephalosporinsfrom6aminopenicillanicacid AT baldwinj synthesesof6scephalosporinsfrom6aminopenicillanicacid AT adlingtonr synthesesof6scephalosporinsfrom6aminopenicillanicacid AT jonest synthesesof6scephalosporinsfrom6aminopenicillanicacid AT proutc synthesesof6scephalosporinsfrom6aminopenicillanicacid AT schofieldc synthesesof6scephalosporinsfrom6aminopenicillanicacid |