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Issue 74, 2012
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(−)-(S)-Nakinadine B: first asymmetric synthesis

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Abstract

(−)-(S)-Nakinadine B has been synthesized for the first time (in 9 steps and 17% overall yield from commercially available atropic acid) using the conjugate addition of lithium dibenzyl-amide to an N-α-phenylacryloyl SuperQuat derivative with in situ diastereoselective enolate protonation as the key step.

Graphical abstract: (−)-(S)-Nakinadine B: first asymmetric synthesis

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Publication details

The article was received on 05 Jul 2012, accepted on 18 Jul 2012 and first published on 25 Jul 2012


Article type: Communication
DOI: 10.1039/C2CC34808J
Citation: Chem. Commun., 2012,48, 9236-9238
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    (−)-(S)-Nakinadine B: first asymmetric synthesis

    S. G. Davies, J. A. Lee, P. M. Roberts, R. S. Shah and J. E. Thomson, Chem. Commun., 2012, 48, 9236
    DOI: 10.1039/C2CC34808J

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