Mild and Rapid Method for the Generation of ortho-(Naphtho)quinone Methide Intermediates (Journal article)

Shaikh, A. K./ Cobb, A. J. A./ Varvounis, G.

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.
Institution and School/Department of submitter: Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας
Keywords: o-quinone methides,diels-alder reactions,aqueous-solution,biomimetic synthesis,efficient method,cross-linking,derivatives,tautomerization,photogeneration,(+/-)-alboatrin
URI: https://olympias.lib.uoi.gr/jspui/handle/123456789/8482
ISSN: 1523-7060
Link: <Go to ISI>://000299238600041
http://pubs.acs.org/doi/pdfplus/10.1021/ol203196n
Publisher: American Chemical Society
Appears in Collections:Άρθρα σε επιστημονικά περιοδικά ( Ανοικτά)

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