Issue 51, 2012
From the journal:

Chemical Communications

Synthesis of the anti-trypanosomal agent (±)-hydroxyanthecotulide by Cr(ii)-catalysed allylation and Meyer–Schuster rearrangement†‡

David M. Hodgson,*a   Eric P. A. Talbota  and  Barry P. Clarkb  

* Corresponding authors

a Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, UK
E-mail: david.hodgson@chem.ox.ac.uk
Fax: +44 (0)1865 285002
Tel: +44 (0)1865 275697

b LRL, Eli Lilly and Co. Ltd, Erl Wood Manor, Windlesham, Surrey, UK

Abstract

The first synthesis of the bioactive sesquiterpene lactone hydroxyanthecotulide is achieved in 7 steps, involving a stereocontrolled Cr(II)-catalysed reaction of 3-(bromomethyl)furan-2(5H)-one with enynal 9 and a mild Au(I)-catalysed Meyer–Schuster rearrangement.

Graphical abstract: Synthesis of the anti-trypanosomal agent (±)-hydroxyanthecotulide by Cr(ii)-catalysed allylation and Meyer–Schuster rearrangement

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Article information

DOI
https://doi.org/10.1039/C2CC32283H
Article type
Communication
Submitted
29 Mar 2012
Accepted
02 May 2012
First published
22 May 2012

Chem. Commun., 2012,48, 6349-6350

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Synthesis of the anti-trypanosomal agent (±)-hydroxyanthecotulide by Cr(II)-catalysed allylation and Meyer–Schuster rearrangement

D. M. Hodgson, E. P. A. Talbot and B. P. Clark, Chem. Commun., 2012, 48, 6349 DOI: 10.1039/C2CC32283H

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