A powerful o-quinone dimethide strategy for intermolecular Diels-Alder cycloadditions Journal Article
| Authors: | Allen, J.; Hentemann, M. F.; Danishefsky, S. J. |
| Article Title: | A powerful o-quinone dimethide strategy for intermolecular Diels-Alder cycloadditions |
| 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. |
| Keywords: | drug synthesis; quinone derivative; chemical structure; idarubicin; oxidation; reaction analysis; chemical reaction; stereochemistry; naphthalene derivative; temperature dependence; article; 1,4 naphthoquinone derivative; idarubicin derivative |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 122 |
| Issue: | 4 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 2000-02-02 |
| Start Page: | 571 |
| End Page: | 575 |
| Language: | English |
| DOI: | 10.1021/ja993627u |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Export Date: 18 November 2015 -- Source: Scopus |
