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. 2012 Jan 20;14(2):584-7.
doi: 10.1021/ol203196n. Epub 2012 Jan 10.

Mild and rapid method for the generation of ortho-(naphtho)quinone methide intermediates

Abdul kadar Shaikh  1 , Alexander J A Cobb, George Varvounis
Affiliations

Mild and rapid method for the generation of ortho-(naphtho)quinone methide intermediates

Abdul kadar Shaikh et al. Org Lett. .

Erratum in

  • Org Lett. 2012 Feb 17;14(4):1183

Abstract

A new mild method has been devised for generating o-(naphtho)quinone methides via fluoride-induced desilylation of silyl derivatives of o-hydroxybenzyl(or 1-naphthylmethyl) nitrate. The reactive o-(naphtho)quinone methide intermediates were trapped by C, O, N, and S nucleophiles and underwent "inverse electron-demand" hetero-Diels-Alder reaction with dienophiles to give stable adducts. The method has useful potential application in natural product synthesis and drug research.

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