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Synthesis of 14C-labeled benzofurano[2,3-b] benzopyran-6-one and its 4-hydroxycoumarin derivative

✍ Scribed by Mitsuo Chubachi; Eiko Kawano

Publisher: John Wiley and Sons
Year: 1987
Tongue: French
Weight: 250 KB
Volume: 24
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580240710

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✦ Synopsis

Isopropyl

-8,9-dimethoxy-benzofurano[2~3-bJfuro[2,3-hJ[ll [ 1 1 -"C]benzopyran-6-one(IVb) and 3-(2-hydroxy-4,5-~~methoxyphenyl)-4-hydroxy-5'-isopropylfurano[2',3':7,8][2-C]coumarin(Vb) were prepared from isorotenone(1b) for use in metabolic and other studies. Deoxybenzoin derivat've(IIb), obtained from isorotenone, was reacted with ethyl["C]fo ate in the presence of sodium to give the corresponding [2-"C]hydroxyisoflavone(IIIb), which was transformed into the "-C-labeled benzofuranor 2,3-b I f uro[ 2,3-h I benzopyran-6-one compound (IVb) by the subsequent oxidative cyclization with selenium dioxide. Hydrolysis of compound IVb in alkaline media gave "C-labeled 4-hydroxycoumarin(Vb).

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