Asymmetric syntheses of moiramide B and andrimid
The first highly diastereoselective asymmetric syntheses of moiramide B 2 and andrimid 3 have been achieved using lithium amide (R)-6 and pyrrolidinone auxiliary (R)-9. Pyrrolidinone auxiliary (R)-9 was used to create the novel (S)-3-methyl-N-benzyloxysuccinimide (S)-11 which was subsequently acylat...
| Main Authors: | , |
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| Format: | Journal article |
| Language: | English |
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1998
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| _version_ | 1797097405146988544 |
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| author | Davies, S Dixon, D |
| author_facet | Davies, S Dixon, D |
| author_sort | Davies, S |
| collection | OXFORD |
| description | The first highly diastereoselective asymmetric syntheses of moiramide B 2 and andrimid 3 have been achieved using lithium amide (R)-6 and pyrrolidinone auxiliary (R)-9. Pyrrolidinone auxiliary (R)-9 was used to create the novel (S)-3-methyl-N-benzyloxysuccinimide (S)-11 which was subsequently acylated with the highly reactive tert-butoxycarbonyl-protected N-carboxy anhydride of L-valine (Boc-val-NCA) (S)-19 under strongly basic conditions, without racemisation. Lithium amide (R)-6 was used to synthesise homochiral D-β-phenylalanine tert-butyl ester 25. |
| first_indexed | 2024-03-07T04:55:01Z |
| format | Journal article |
| id | oxford-uuid:d64be73e-7bb5-4a0c-91c6-0a4eaa812337 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T04:55:01Z |
| publishDate | 1998 |
| record_format | dspace |
| spelling | oxford-uuid:d64be73e-7bb5-4a0c-91c6-0a4eaa8123372022-03-27T08:32:27ZAsymmetric syntheses of moiramide B and andrimidJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:d64be73e-7bb5-4a0c-91c6-0a4eaa812337EnglishSymplectic Elements at Oxford1998Davies, SDixon, DThe first highly diastereoselective asymmetric syntheses of moiramide B 2 and andrimid 3 have been achieved using lithium amide (R)-6 and pyrrolidinone auxiliary (R)-9. Pyrrolidinone auxiliary (R)-9 was used to create the novel (S)-3-methyl-N-benzyloxysuccinimide (S)-11 which was subsequently acylated with the highly reactive tert-butoxycarbonyl-protected N-carboxy anhydride of L-valine (Boc-val-NCA) (S)-19 under strongly basic conditions, without racemisation. Lithium amide (R)-6 was used to synthesise homochiral D-β-phenylalanine tert-butyl ester 25. |
| spellingShingle | Davies, S Dixon, D Asymmetric syntheses of moiramide B and andrimid |
| title | Asymmetric syntheses of moiramide B and andrimid |
| title_full | Asymmetric syntheses of moiramide B and andrimid |
| title_fullStr | Asymmetric syntheses of moiramide B and andrimid |
| title_full_unstemmed | Asymmetric syntheses of moiramide B and andrimid |
| title_short | Asymmetric syntheses of moiramide B and andrimid |
| title_sort | asymmetric syntheses of moiramide b and andrimid |
| work_keys_str_mv | AT daviess asymmetricsynthesesofmoiramidebandandrimid AT dixond asymmetricsynthesesofmoiramidebandandrimid |