Asymmetric synthesis of the marine alkaloid (−)-(S)-nakinadine C |
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Authors: | Stephen G. Davies Paul M. RobertsRushabh S. Shah James E. Thomson |
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Affiliation: | Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK |
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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. |
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Keywords: | Alkaloid Conjugate addition Nakinadine SuperQuat |
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