82448-67-7Relevant academic research and scientific papers
Regioselective synthesis of prenylisoflavones. Syntheses of allolicoisoflavone A, 2,3-dehydrokievitone, and related compounds
Tsukayama, Masao,Li, He,Tsurumoto, Ken,Nishiuchi, Masaki,Kawamura, Yasuhiko
, p. 2673 - 2680 (2007/10/03)
The palladium-catalyzed coupling reaction of 2',4',5,7- tetrakis(benzyloxy)-5'-iodolsoflavone (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.
Synthesis of Licoisoflavone A and Related Compounds
Tsukayma, Masao,Fujimoto, Kunihiro,Horie, Tokunaru,Masumura, Mitsuo,Nakayama, Mitsuru
, p. 136 - 141 (2007/10/02)
2',4',5,7-Tetrahydroxyisoflavone was partially benzoylated with benzoyl chloride to give 7-benzoyloxy-2',4',5-trihydroxyisoflavone.The condensation of the 7-(benzoyloxy)isoflavone with 2-methyl-3-buten-2-ol, followed by the hydrolysis of the resultant 3'-(3-methyl-2-butenyl)isoflavone gave licoisoflavone A.Its 5'-(3-methyl-2-butenyl) isomer was also synthesized from 5-benzoyloxy-2',4',7-trihydroxyisoflavone in a similar manner.
SYNTHESES OF LICOISOFLAVONE A AND 5'-ALKENYL ISOMER
Tsukayama, Masao,Fujimoto, Kunihiro,Horie, Tokunaru,Yamashita, Yoshiro,Masumura, Mitsuo,Nakayama, Mitsuru
, p. 675 - 678 (2007/10/02)
2',4',5,7-Tetrahydroxyisoflavone was partially benzoylated with benzoyl chloride to give 7-benzoyloxy-2',4',5-trihydroxyisoflavone.The condensation of 7-benzoyloxyisoflavone with 2-methyl-3-buten-2-ol, followed by the hydrolysis of the resultant 3'-(3-met
