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KMID : 0043320080310121559
Archives of Pharmacal Research
2008 Volume.31 No. 12 p.1559 ~ p.1563
Concise Synthesis of Obovatol: Chemoselective ortho-Bromination of Phenol and Survey of Cu-Catalyzed Diaryl Ether Couplings
Jung Jae-Kyeong


Hong Jin-Tae
Lee Hee-Soon
Lee Soo-Jae
Yoon Yeo-Pyo
Seo Seung-Yong
Choi Eun-Hwa
Lee Mi-Sung
In Jin-Kyung
Kwak Jae-Hwan
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.
KEYWORD
Obovatol, ortho-Bromination, Ullmann coupling, Diaryl ether
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