Issue 14, 2005
From the journal:

Chemical Communications

Synthesis of a simplified analogue of eleutherobin via a Claisen rearrangement and ring closing metathesis strategy†

Gary C. H. Chiang,a   Andrew D. Bond,a   Andrew Ayscough,b   Gilles Pain,b   Sylvie Duckic  and  Andrew B. Holmes*ad  

* Corresponding authors

a Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK
E-mail: abh1@cam.ac.uk, aholmes@unimelb.edu.au

b British Biotech Pharmaceuticals Ltd., Watlington Road, Oxford, UK

c Centre for Molecular Drug Design, Cockroft Building, University of Salford, Salford, UK

d Bio21 Institute, University of Melbourne, Parkville Vic. 3010, Australia

Abstract

The enantioselective synthesis of a simplified eleutherobin analogue 7 by ring closing metathesis (RCM) of the 2,9-divinyl-substituted tetrahydro-oxonin 5 is described; the analogue 7 and an advanced intermediate 15 revealed microtubule stabilising properties in the micromolar range.

Graphical abstract: Synthesis of a simplified analogue of eleutherobin via a Claisen rearrangement and ring closing metathesis strategy

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Article information

DOI
https://doi.org/10.1039/B413426E
Article type
Communication
Submitted
02 Sep 2004
Accepted
13 Dec 2004
First published
11 Feb 2005

Chem. Commun., 2005, 1860-1862

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Synthesis of a simplified analogue of eleutherobin via a Claisen rearrangement and ring closing metathesis strategy

G. C. H. Chiang, A. D. Bond, A. Ayscough, G. Pain, S. Ducki and A. B. Holmes, Chem. Commun., 2005, 1860 DOI: 10.1039/B413426E

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