Issue 23, 2011
From the journal:

Organic & Biomolecular Chemistry

Transannular Claisen rearrangement reactions for the synthesis of vinylcyclobutanes: formal synthesis of (±)-grandisol†

Donald Craig,*a   Kiyohiko Funai,a   Sophie J. Gore,a   Albert Kanga  and  Alexander V. W. Maywegb  

* Corresponding authors

a Department of Chemistry, Imperial College London, South Kensington Campus, London, UK
E-mail: d.craig@imperial.ac.uk
Fax: +44 (0)20 7594 5804
Tel: +44 (0)20 7594 5771

b F. Hoffmann–La Roche Ltd, Pharmaceuticals Division, Grenzacherstrasse 124, Switzerland

Abstract

Unsaturated eight-membered lactones undergo decarboxylative and non-decarboxylative transannular Ireland–Claisen rearrangement reactions, to give substituted vinylcyclobutanes. A formal synthesis of (±)-grandisol is described.

Graphical abstract: Transannular Claisen rearrangement reactions for the synthesis of vinylcyclobutanes: formal synthesis of (±)-grandisol

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Article information

DOI
https://doi.org/10.1039/C1OB06619F
Article type
Communication
Submitted
22 Sep 2011
Accepted
06 Oct 2011
First published
06 Oct 2011

Org. Biomol. Chem., 2011,9, 8000-8002

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Transannular Claisen rearrangement reactions for the synthesis of vinylcyclobutanes: formal synthesis of (±)-grandisol

D. Craig, K. Funai, S. J. Gore, A. Kang and A. V. W. Mayweg, Org. Biomol. Chem., 2011, 9, 8000 DOI: 10.1039/C1OB06619F

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