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Asymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine C

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

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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:

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