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DOI: 10.1039/A709191E (Paper) Reference Section for: J. Chem. Res. (S), 1998, 238-239

Regioselective Synthesis of Prenylisoflavones. Syntheses of Lupiwighteone, Lupiwighteone Hydrate and Related Compounds

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Masao Tsukayama, He Li, Masaki Nishiuchi, Masahumi Takahashi and Yasuhiko Kawamura

Abstract

Catalytic hydrogenation and the subsequent dehydration of 8-(3-hydroxy-3-methylbutynyl)isoflavone 12, which was synthesized by the palladium-catalyzed coupling reaction of 4′,5,7-tris(benzyloxy)-8-iodoisoflavone 11 with 2-methyl-3-butyn-2-ol, gave a mixture of 8-prenylisoflavone 16 and the isomer [5-acetoxy-8-(3-methyl-3-butenyl)isoflavone] 17, and after the separation of 16 was accomplished by treatment of the mixture with Hg(NO3)2, hydrolysis of 16 afforded 4′,5,7-trihydroxy-8-prenylisoflavone (lupiwighteone) 1.

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