Journal
TETRAHEDRON LETTERS
Volume 52, Issue 17, Pages 2268-2271Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.02.016
Keywords
Regioselective ring-opening; Hetero Diels-Alder; Bisaryl ether; Transcarbamoylation; Lipoxygenase
Categories
Funding
- NIH [GM068012]
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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 that the compounds may possess significant inhibitory potency against the proinflammatory enzyme 5-lipoxygenase. (C) 2011 Elsevier Ltd. All rights reserved.
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