A Powerful o-Quinone Dimethide Strategy for Intermolecular Diels−Alder Cycloadditions
Journal of the American Chemical Society2000Vol. 122(4), pp. 571–575
Citations Over TimeTop 10% of 2000 papers
Abstract
Conrotatory thermal fragmentation of trans-1,2-disilyloxybenzocyclobutenes generates o-quinone dimethides at remarkably low temperatures. Smooth stereoselective Diels−Alder cycloaddition with a range of dienophiles provides hydronaphthalene derivatives in excellent yield. Direct oxidative desilylation of the adducts affords the corresponding naphthoquinones. Substitution of the benzene nucleus with an electron-releasing methoxyl group directs the cycloaddition to give good control of regioselectivity in the expected direction. A short synthesis of the aglycon of the anticancer antibiotic idarubicin is presented.
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