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Paper | Regular issue | Vol 65, No. 7, 2005, pp.1641-1654
Published online, 28th April, 2005
DOI: 10.3987/COM-05-10424
A Short-step Convenient Synthesis of 2-Phenylbenzofuran from 3-Phenylcoumarin

Takeshi Kinoshita* and Koji Ichinose

*Faculty of Pharmaceutical Sciences, Teikyo University, 1091-1 Suarashi, Sagamiko-machi, Tsukui-gun, Kanagawa 199-0195, Japan


The reaction mechanism of chemical conversion of (E)-β-[2-hydroxylphenylethylene]benzeneethanol into 2-phenylbenzofuran by DDQ, which involves loss of one carbon unit, was characterized and described. Five naturally occurring 2-phenylbenzofurans of not only the isoflavonoid but also stilbenoid origin were synthesized by use of this chemical scheme, which proved that this new scheme is a useful tool for quick synthesis of 2-phenylbenzofurans.