- Abstract:
- 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.
- Publication status:
- Published
- Publisher copy:
- 10.1016/j.tetlet.2013.09.043
-
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- Journal:
- TETRAHEDRON LETTERS
- Volume:
- 54
- Issue:
- 48
- Pages:
- 6423-6426
- Publication date:
- 2013-11-27
- DOI:
- EISSN:
-
1873-3581
- ISSN:
-
0040-4039
- URN:
-
uuid:9bc765b5-eb3d-49e6-aadf-d7abdd5038c7
- Source identifiers:
-
435476
- Local pid:
- pubs:435476
- Language:
- English
- Keywords:
- Copyright date:
- 2013
Journal article
Asymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine C
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