Issue 9, 2006
From the journal:

Organic & Biomolecular Chemistry

A highly enantioselective total synthesis of (+)-goniodiol

Edward W. Tate,a   Darren J. Dixonb  and  Steven V. Ley*c  

* Corresponding authors

a Biological and Biophysical Chemistry Section, Department of Chemistry, Imperial College London, London, UK
E-mail: e.tate@imperial.ac.uk
Fax: +44 20 7594 1139
Tel: +44 20 7594 5720

b Department of Chemistry, The University of Manchester, Manchester, UK
E-mail: Darren.Dixon@man.ac.uk
Fax: +44 161 2754939
Tel: +44 161 2751426

c Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK
E-mail: svl1000@cam.ac.uk
Fax: +44 1223 336442
Tel: +44 1223 336398

Abstract

A high-yielding enantioselective total synthesis of the bioactive styryllactone (+)-goniodiol has been realised, starting from readily available (S)-glycidol. A key step is an oxygen-to-carbon rearrangement of a silyl enol ether linked via an anomeric centre, facilitating the rapid and diastereoselective construction of this functionalised system.

Graphical abstract: A highly enantioselective total synthesis of (+)-goniodiol

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Article information

DOI
https://doi.org/10.1039/B602805E
Article type
Paper
Submitted
23 Feb 2006
Accepted
09 Mar 2006
First published
27 Mar 2006

Org. Biomol. Chem., 2006,4, 1698-1706

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A highly enantioselective total synthesis of (+)-goniodiol

E. W. Tate, D. J. Dixon and S. V. Ley, Org. Biomol. Chem., 2006, 4, 1698 DOI: 10.1039/B602805E

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