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Issue 98, 2015
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An ortho-quinone methide based strategy towards the rubromycin spiroketal family

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Abstract

A method for the generation/in situ hetero-Diels–Alder cycloaddition of a trisubstituted ortho-quinone methide (o-QM) is described. Heating of ortho-hydroxybenzylamines was found to be a more effective strategy for the formation of o-QMs than use of the corresponding N-substituted quaternary salts hitherto employed. This method was used to synthesise the spiroketal core of the rubromycins.

Graphical abstract: An ortho-quinone methide based strategy towards the rubromycin spiroketal family

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Publication details

The article was received on 24 Aug 2015, accepted on 09 Sep 2015 and first published on 10 Sep 2015


Article type: Communication
DOI: 10.1039/C5RA17108C
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Citation: RSC Adv., 2015,5, 80212-80215
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    An ortho-quinone methide based strategy towards the rubromycin spiroketal family

    N. J. Willis and C. D. Bray, RSC Adv., 2015, 5, 80212
    DOI: 10.1039/C5RA17108C

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