Issue 15, 2008
From the journal:

Organic & Biomolecular Chemistry

Generation and hetero-Diels–Alder reactions of an o-quinone methide under mild, anionic conditions: rapid synthesis of mono-benzannelated spiroketals†

Christopher D. Bray*a  

* Corresponding authors

a School of Biological and Chemical Sciences, The Walter Besant Building, Queen Mary, University of London, Mile End Road, London, United Kingdom
E-mail: c.bray@qmul.ac.uk
Fax: +44 (0)20 7882 7427
Tel: +44 (0)20 7882 3271

Abstract

Deprotonation of o-hydroxybenzyl acetate with iPrMgCl provides a method of generating an o-quinone methide under mild, anionic conditions, such that highly sensitive exo-enol ethers can be employed as 2π partners in hetero-Diels–Alder reactions. This process results in mono-benzannelated spiroketals such as those found in the natural products berkelic acid, the chaetoquadrins or cephalostatin 6.

Graphical abstract: Generation and hetero-Diels–Alder reactions of an o-quinone methide under mild, anionic conditions: rapid synthesis of mono-benzannelated spiroketals

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Article information

DOI
https://doi.org/10.1039/B806593D
Article type
Paper
Submitted
21 Apr 2008
Accepted
23 Apr 2008
First published
28 May 2008

Org. Biomol. Chem., 2008,6, 2815-2819

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Generation and hetero-Diels–Alder reactions of an o-quinone methide under mild, anionic conditions: rapid synthesis of mono-benzannelated spiroketals

C. D. Bray, Org. Biomol. Chem., 2008, 6, 2815 DOI: 10.1039/B806593D

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