Issue 4, 2008
From the journal:

Organic & Biomolecular Chemistry

The Claisen rearrangement approach to fused bicyclic medium-ring oxacycles†‡§

Jonathan W. Burton,*ab   Edward A. Anderson,a   Paul T. O'Sullivan,a   Ian Collins,c   John E. Davies,a   Andrew D. Bond,a   Neil Feedera  and  Andrew B. Holmes*ad  

* Corresponding authors

a Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK

b Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, UK
E-mail: jonathan.burton@chem.ox.ac.uk

c The Institute of Cancer Research, 15 Cotswold Road, Sutton, UK

d School of Chemistry, Bio21 Institute, University of Melbourne, Victoria, Australia
E-mail: aholmes@unimelb.edu.au

Abstract

The synthesis of five fused-bicyclic medium-ring lactones carrying identical ring-fusion to that in the polyether toxins is described using an enolate hydroxylation, intramolecular hydrosilation, Claisen rearrangement sequence.

Graphical abstract: The Claisen rearrangement approach to fused bicyclic medium-ring oxacycles

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Article information

DOI
https://doi.org/10.1039/B715354F
Article type
Paper
Submitted
05 Oct 2007
Accepted
30 Nov 2007
First published
04 Jan 2008

Org. Biomol. Chem., 2008,6, 693-702

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The Claisen rearrangement approach to fused bicyclic medium-ring oxacycles

J. W. Burton, E. A. Anderson, P. T. O'Sullivan, I. Collins, J. E. Davies, A. D. Bond, N. Feeder and A. B. Holmes, Org. Biomol. Chem., 2008, 6, 693 DOI: 10.1039/B715354F

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