Issue 4, 2000
From the journal:

Chemical Communications

Synthesis of (±)-kainic acid by dearomatising cyclisation of a lithiated N-benzyl p-anisamide

Jonathan Clayden*a  and  Kirill Tchabanenkoa  

* Corresponding authors

a Department of Chemistry, University of Manchester, Oxford Road, Manchester, UK
E-mail: j.p.clayden@man.ac.uk

Abstract

N-Benzyl p-anisamide 6, on lithiation with ButLi in the presence of HMPA, undergoes a stereoselective anionic cyclisation with loss of aromaticity to give a bicyclic enone which may be converted in nine steps to (±)-kainic acid.

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Article information

DOI
https://doi.org/10.1039/A909325G
Article type
Communication
Submitted
24 Nov 1999
Accepted
12 Jan 2000
First published
10 Feb 2000

Chem. Commun., 2000, 317-318

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Synthesis of (±)-kainic acid by dearomatising cyclisation of a lithiated N-benzyl p-anisamide

J. Clayden and K. Tchabanenko, Chem. Commun., 2000, 317 DOI: 10.1039/A909325G

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