Mild and rapid method for the generation of ortho-(naphtho)quinone methide intermediates.
| Autor: | Shaikh Ak; Department of Chemistry, University of Ioannina, Section of Organic Chemistry and Biochemistry, 451 10 Ioannina, Greece., Cobb AJ, Varvounis G |
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| Jazyk: | angličtina |
| Zdroj: | Organic letters [Org Lett] 2012 Jan 20; Vol. 14 (2), pp. 584-7. Date of Electronic Publication: 2012 Jan 10. |
| DOI: | 10.1021/ol203196n |
| Abstrakt: | 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. (© 2012 American Chemical Society) |
| Databáze: | MEDLINE |
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