A Convenient Synthesis of Prenylated Isoflavones : Synthesis of Licoricone and Related Compounds

The condensation of 6', 7-bis(benzoyloxy)-2', 4'-dimethoxyisolfavone (18) with 2-methyl-3-buten-2-ol, followed by hydrolysis of the resultant 6', 7-bis(benzoyloxy)-2', 4'-dimethoxy-3'-(3-methyl-2-butenyl)isoflavone (19) gave 6', 7-dihydroxy-2', 4'-di...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1986/06/25, Vol.34(6), pp.2369-2374
Hauptverfasser: TSUKAYAMA, MASAO, HORIE, TOKUNARU, FUJIMOTO, KUNIHIRO, NAKAYAMA, MITSURU
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Sprache:eng
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Zusammenfassung:The condensation of 6', 7-bis(benzoyloxy)-2', 4'-dimethoxyisolfavone (18) with 2-methyl-3-buten-2-ol, followed by hydrolysis of the resultant 6', 7-bis(benzoyloxy)-2', 4'-dimethoxy-3'-(3-methyl-2-butenyl)isoflavone (19) gave 6', 7-dihydroxy-2', 4'-dimethoxy-3'-(3-methyl-2-butenyl)-isoflavone (licoricone) (1). Its isomer, 6', 7-dihydroxy-2', 4'-dimethoxy-5'-(3-methyl-2-butenyl)-isoflavone (2), was also synthesized from 7-benzoyloxy-6'-hydroxy- or 6', 7-bis(benzoyloxy)-2', 4'-dimethoxy-5'-(3-methyl-2-butenyl)isoflavone (11 or 20).
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.34.2369