Studies on macrocyclic lactone antibiotics. XIII. Anti-tubulin activity and cytotoxicity of rhizoxin derivatives: synthesis of a photoaffinity derivative.

@article{Kato1991StudiesOM,
  title={Studies on macrocyclic lactone antibiotics. XIII. Anti-tubulin activity and cytotoxicity of rhizoxin derivatives: synthesis of a photoaffinity derivative.},
  author={Y Kato and Yuka Ogawa and Takuma Imada and S Iwasaki and Noboru Shimazaki and T Kobayashi and Toru Komai},
  journal={The Journal of antibiotics},
  year={1991},
  volume={44 1},
  pages={
          66-75
        }
}
Chemical modification of the side chain in rhizoxin, a potent antimitotic agent, was attempted in order to study structure-activity relationships and also to devise a probe for photoaffinity labeling of tubulin. An OsO4/NaIO4 oxidation gave a nor-rhizoxin 20-al (5) which was converted to 20-ol (6) by a NaBH3CN reduction. Starting from these two compounds as key intermediates, a series of Wittig reaction products 7-2, and of 20-O-acylates 13-21 were prepared and their anti-tubulin activity and… 

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