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Issue 15, 2008
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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

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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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Publication details

The article was received on 21 Apr 2008, accepted on 23 Apr 2008 and first published on 28 May 2008


Article type: Paper
DOI: 10.1039/B806593D
Citation: 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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