Issue 74, 2012
From the journal:

Chemical Communications

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

Stephen G. Davies,*a   James A. Lee,a   Paul M. Roberts,a   Rushabh S. Shaha  and  James E. Thomsona  

* Corresponding authors

a 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

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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Article information

DOI
https://doi.org/10.1039/C2CC34808J
Article type
Communication
Submitted
05 Jul 2012
Accepted
18 Jul 2012
First published
25 Jul 2012

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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