Regioselective Synthesis of Prenylisoflavones. Syntheses of Allolicoisoflavone A, 2,3-Dehydrokievitone, and Related Compounds.

@article{Tsukayama1998RegioselectiveSO,
  title={Regioselective Synthesis of Prenylisoflavones. Syntheses of Allolicoisoflavone A, 2,3-Dehydrokievitone, and Related Compounds.},
  author={M. Tsukayama and He Li and Ken Tsurumoto and M. Nishiuchi and Y. Kawamura},
  journal={Bulletin of the Chemical Society of Japan},
  year={1998},
  volume={71},
  pages={2673-2680}
}
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… Expand
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