Issue 74, 2012

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

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

Supplementary files

Article information

Article type
Communication
Submitted
05 Jul 2012
Accepted
18 Jul 2012
First published
25 Jul 2012

Chem. Commun., 2012,48, 9236-9238

(−)-(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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