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Arch Pharm Res. 2008 Dec;31(12):1559-63. doi: 10.1007/s12272-001-2151-9. Epub 2008 Dec 20.

Concise synthesis of Obovatol: Chemoselective ortho-bromination of phenol and survey of Cu-catalyzed diaryl ether couplings.

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  • 1College of Pharmacy, CBITRC, Chungbuk National University, Cheongju, 361-763, Korea.

Abstract

Concise total synthesis of obovatol (1) was achieved from the commercially available eugenol (5) via linear 4 steps in 40% overall yield. The key features of the synthesis involve the chemoselective orthobromination of phenol in the presence of isolated double bond and the efficient Cu-catalyzed Ullmann coupling of two aromatic moieties for the diaryl ether skeleton.

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