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Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, UK
E-mail: steve.davies@chem.ox.ac.uk
; Fax: +44 (0)1865 275633
; Tel: +44 (0)1865 275695
Chem. Commun., 2012,48, 9236-9238
DOI:
10.1039/C2CC34808J
Received
05 Jul 2012,
Accepted
18 Jul 2012
First published online
25 Jul 2012
(−)-(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.