Tsukayama Masao, Wada Hironari, Kawamura Yasuhiko, Yamashita Kazuyo, Nishiuchi Masaki
Department of Chemical Science and Technology, Faculty of Engineering, The University of Tokushima, Minamijosanjima-cho, Tokushima 770-8506, Japan.
Chem Pharm Bull (Tokyo). 2004 Nov;52(11):1285-9. doi: 10.1248/cpb.52.1285.
The palladium-catalyzed coupling reaction of 6-iodoisoflavone, prepared from 3'-iodoacetophenone derivative, with 2-methyl-3-butyn-2-ol gave 6-alkynylisoflavone derivative, which was hydrogenated to give 6-alkylhydroxyisoflavone (luteone hydrate) (2). Dehydration of 2 gave 2',4',5,7-tetrahydroxy-6-prenylisoflavone (luteone) (1). Wighteone hydrate (3) was also synthesized from 6-iodotris(benzyloxy)isoflavone in a similar manner. 6-Alkyl-4'5,7-trihydroxy-coumaronochromone (4) was synthesized by oxidative cyclization of 2 with o-chloranil.
由3'-碘苯乙酮衍生物制备的6-碘异黄酮与2-甲基-3-丁炔-2-醇的钯催化偶联反应得到6-炔基异黄酮衍生物，该衍生物经氢化得到6-烷基羟基异黄酮（水合黄烷酮）（2）。2脱水得到2',4',5,7-四羟基-6-异戊烯基异黄酮（黄烷酮）（1）。水合白檀酮（3）也以类似方式由6-碘三（苄氧基）异黄酮合成。通过用邻氯苯醌将2氧化环化合成了6-烷基-4',5,7-三羟基香豆素色原酮（4）。
