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

descriptionPublicationkeyboard_double_arrow_right Article 01 Jan 1998Publisher:Royal Society of Chemistry (RSC)Journal:Journal of Chemical Research (issn: 0308-2342, eissn: 1364-5560,

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Authors: Masao Tsukayama; He Li; Masaki Nishiuchi; Masahumi Takahashi; Yasuhiko Kawamura;

doi: 10.1039/a709191e

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

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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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