Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Regioselective Synthesis of Prenylisoflavones. Syntheses of Allolicoisoflavone A, 2,3-Dehydrokievitone, and Related Compounds
Masao TsukayamaHe LiKen TsurumotoMasaki NishiuchiYasuhiko Kawamura
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1998 Volume 71 Issue 11 Pages 2673-2680

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Abstract

The palladium-catalyzed coupling reaction of 2′,4′,5,7-tetrakis(benzyloxy)-5′-iodoisoflavone (12), synthesized from the 5-iodochalcone 9, with 2-methyl-3-butyn-2-ol gave the corresponding 5′-(3-hydroxy-3-methyl-1-butynyl)isoflavone 13. The catalytic hydrogenation of 13 gave 2′,4′,5,7-tetrahydroxy-5′-(3-hydroxy-3-methylbutyl)isoflavone (2). Dehydration of the benzoate 14 of 2 afforded a mixture of 5′-(3-methyl-2-butenyl)isoflavone 15 and the isomer 5′-(3-methyl-3-butenyl)isoflavone 16. The separation of 15 was accomplished by a treatment of the mixture (15 and 16) with mercury(II) nitrate. Hydrolysis of 15 afforded 2′,4′,5,7-tetrahydroxy-5′-prenylisoflavone (allolicoisoflavone A) (1). In a similar manner, 2′,4′,5,7-tetrahydroxy-8-prenylisoflavone (2,3-dehydrokievitone) (3) and 2′,4′,5,7-tetrahydroxy-8-(3-hydroxy-3-methylbutyl)isoflavone (2,3-dehydrokievitone hydrate) (4) were synthesized from the corresponding 8-iodoisoflavone 22. The tetramethyl ether 5 of 3 was also prepared from the 8-iodotetramethoxyisoflavone 32.

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© 1998 The Chemical Society of Japan
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