Issue 1, 2007
From the journal:

Organic & Biomolecular Chemistry

Stereoselective synthesis, natural occurrence and CB2 receptor binding affinities of alkylamides from herbal medicines such as Echinacea sp.

N. Matovic,a   A. Matthias,b   Jürg Gertsch,c   Stefan Raduner,c   K. M. Bone,bd   R. P. Lehmannb  and  J. J. DeVoss*a  

* Corresponding authors

a Chemistry, School of Molecular and Microbial Sciences, The University of Queensland, Brisbane, Australia
E-mail: j.devoss@uq.edu.au
Fax: +61 7 3365 4299
Tel: +61 7 3365 3825

b MediHerb Research Laboratories, 3/85 Brandl Street, Eight Mile Plains, Australia
E-mail: reg@mediherb.com.au
Fax: +61734236599
Tel: +61734236521

c Department of Chemistry and Applied Biosciences, ETH Zürich, Zürich, Switzerland
E-mail: juerg.gertsch@pharma.ethz.ch
Fax: +41446331366
Tel: +41446337374

d School of Health, University of New England, Armidale, Australia
Fax: +61746610788
Tel: +61746610700

Abstract

A divergent synthesis of (2E,4E,8E,10E)- and (2E,4E,8E,10Z)-N-isobutyldodeca-2,4,8,10-tetraenamides from pent-4-yn-1-ol allowed identification of the (2E,4E,8E,10Z)-isomer for the first time in Echinacea species. A short, stereoselective synthesis of the (2E,4E,8E,10Z)-isomer is also described which allowed further biological evaluation of this material, and the demonstration that this isomer does not occur in Spilanthes mauritiana as previously reported.

Graphical abstract: Stereoselective synthesis, natural occurrence and CB2 receptor binding affinities of alkylamides from herbal medicines such as Echinacea sp.

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Article information

DOI
https://doi.org/10.1039/B615487E
Article type
Paper
Submitted
25 Oct 2006
Accepted
01 Nov 2006
First published
29 Nov 2006

Org. Biomol. Chem., 2007,5, 169-174

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Stereoselective synthesis, natural occurrence and CB2 receptor binding affinities of alkylamides from herbal medicines such as Echinacea sp.

N. Matovic, A. Matthias, J. Gertsch, S. Raduner, K. M. Bone, R. P. Lehmann and J. J. DeVoss, Org. Biomol. Chem., 2007, 5, 169 DOI: 10.1039/B615487E

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