Asymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine C
The first asymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine C is described. This synthesis employs the conjugate addition of lithium dibenzylamide to an N-α-phenylacryloyl SuperQuat derivative followed by diastereoselective protonation of the intermediate enolate using 2-pyridone as the...
| Main Authors: | , , , |
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| Format: | Journal article |
| Jezik: | English |
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2013
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| _version_ | 1826287272187658240 |
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| author | Davies, S Roberts, P Shah, R Thomson, J |
| author_facet | Davies, S Roberts, P Shah, R Thomson, J |
| author_sort | Davies, S |
| collection | OXFORD |
| description | The first asymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine C is described. This synthesis employs the conjugate addition of lithium dibenzylamide to an N-α-phenylacryloyl SuperQuat derivative followed by diastereoselective protonation of the intermediate enolate using 2-pyridone as the key step to introduce the stereochemistry. (-)-(S)-Nakinadine C was isolated in 13% yield over 9 steps from commercially available atropic acid, 98:2 dr [(Z):(E) ratio] and >99% ee. © 2013 Elsevier Ltd. All rights reserved. |
| first_indexed | 2024-03-07T01:56:10Z |
| format | Journal article |
| id | oxford-uuid:9bc765b5-eb3d-49e6-aadf-d7abdd5038c7 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T01:56:10Z |
| publishDate | 2013 |
| record_format | dspace |
| spelling | oxford-uuid:9bc765b5-eb3d-49e6-aadf-d7abdd5038c72022-03-27T00:31:11ZAsymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine CJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:9bc765b5-eb3d-49e6-aadf-d7abdd5038c7EnglishSymplectic Elements at Oxford2013Davies, SRoberts, PShah, RThomson, JThe first asymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine C is described. This synthesis employs the conjugate addition of lithium dibenzylamide to an N-α-phenylacryloyl SuperQuat derivative followed by diastereoselective protonation of the intermediate enolate using 2-pyridone as the key step to introduce the stereochemistry. (-)-(S)-Nakinadine C was isolated in 13% yield over 9 steps from commercially available atropic acid, 98:2 dr [(Z):(E) ratio] and >99% ee. © 2013 Elsevier Ltd. All rights reserved. |
| spellingShingle | Davies, S Roberts, P Shah, R Thomson, J Asymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine C |
| title | Asymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine C |
| title_full | Asymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine C |
| title_fullStr | Asymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine C |
| title_full_unstemmed | Asymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine C |
| title_short | Asymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine C |
| title_sort | asymmetric synthesis of the marine alkaloid s nakinadine c |
| work_keys_str_mv | AT daviess asymmetricsynthesisofthemarinealkaloidsnakinadinec AT robertsp asymmetricsynthesisofthemarinealkaloidsnakinadinec AT shahr asymmetricsynthesisofthemarinealkaloidsnakinadinec AT thomsonj asymmetricsynthesisofthemarinealkaloidsnakinadinec |