title: Diaryl Ether Containing N-Hydroxycarbamates from Nitroso Cycloadducts.
abstract: Regioselective ring opening of N-hydroxycarbamate-derived nitroso cycloadducts by a copper-catalyzed allylic alkylation reaction was achieved and applied to the synthesis of a set of substituted diaryl ether containing compounds. Use of protected 3-hydroxybenzyl bromide allowed access to a late stage phenol intermediate after protection of the N-hydroxy moiety that was generated from the ring opening reaction. The diaryl ethers were then formed by copper-mediated coupling with arylboronic acids. After selective deprotection, alumina-promoted transcarbamoylation provided the target compounds. Previous results indicate the compounds may possess significant inhibitory potency against the proinflammatory enzyme 5-lipoxygenase.
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556.
authors.forename: Joshua
authors.initials: J
authors.lastname: Bolger
authors.forename: Marvin
authors.initials: M
authors.lastname: Miller