Diaryl ether containing N-hydroxycarbamates from nitroso cycloadducts

作者：Bolger Joshua; Miller Marvin^*

来源：Tetrahedron Letters, 2011, 52(17): 2268-2271.

DOI：10.1016/j.tetlet.2011.02.016

• Regioselective ring-opening
• Hetero Diels-Alder
• Bisaryl ether
• Transcarbamoylation
• Lipoxygenase

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.

• 出版日期2011-4-27