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Efficient Generation of <i>ortho</i>‐Naphthoquinone Methides from 1,4‐Epoxy‐1,4‐dihydronaphthalenes and Their Annulation with Allyl Silanes
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2012
Year
Medicinal ChemistryEfficient GenerationHeterocyclicUseful Dihydronaphthopyran DerivativesDiversity Oriented SynthesisDerivative (Chemistry)Natural SciencesAllyl SilanesFecl3 CatalysisMedicineOrganic ChemistryChemistryHeterocycle ChemistryPharmacologyChemical DerivativeSynthetic ChemistryBiomolecular EngineeringDrug Discovery
Pharmaceutically useful dihydronaphthopyran derivatives were obtained in good yield by the regio- and stereoselective annulation of ortho-naphthoquinone methides with allyl silanes. The ortho-naphthoquinone methides were generated in situ from 1-siloxymethyl-1,4-epoxy-1,4-dihydronaphthalenes under FeCl3 catalysis (see scheme; allyl-TMS=allyltrimethylsilane, TBS=tert-butyldimethylsilyl, TMS=trimethylsilyl). As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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