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

Abdul kadar Shaikh; Alexander J A Cobb; George Varvounis

doi:10.1021/ol203196n

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

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

Authors

Abdul kadar Shaikh¹, Alexander J A Cobb, George Varvounis

Affiliation

¹ Department of Chemistry, University of Ioannina, Section of Organic Chemistry and Biochemistry, 451 10 Ioannina, Greece.

PMID: 22233235
DOI: 10.1021/ol203196n

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Dimerization
Indolequinones / chemical synthesis*
Molecular Structure
Naphthoquinones / chemical synthesis*
Time Factors

Substances

Indolequinones
Naphthoquinones
quinone methide