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Tetrahedron Lett. 2011 Apr 27;52(17):2268-2271.

Diaryl Ether Containing N-Hydroxycarbamates from Nitroso Cycloadducts.

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  • 1Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556.


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.

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