Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of 11-Deoxydaunomycinone and Novel 10-Fluoroanthracyclinone Derivatives

  • Published : 1999.05.20
Download PDF
⟨ Previous Next ⟩

Abstract

11-Deoxydaunomycinone 15 and 10-fluoroanthracyclinone derivatives 9, 10 were obtained. Naphthalenone 4 prepared from 2-(2,4-pentadienyl)-1,3-dioxane 2 with methyl vinyl ketone and hydrolysis with HClO4 was condensed with phthalidesulfone 5 through Michael type reaction, and was converted to 7 by epoxidation. Epoxide 7 was transformed to trione 12 using reduction-oxidation or hydrofluorination process, and then to 15 by introducing several functional groups. Compound 8 obtained in the course of the reaction of epoxide 7 and HF/ Pyr was used for the synthesis of compounds 9, 10.

Keywords

References

  1. Doxorubicin Arcamone, F.
  2. ACS Symposium Series 574 Anthracycline Antibiotics Priebe, W.
  3. Tetrahedron Symposia-in Print No. 17 Recent Aspects of Anthracyclinone Chemistry Kelly, T. R.
  4. Can. J. Chem. v.51 Wong, C. M.;Schwenk, R.;Popein, D.;Ho, T. L.
  5. J. Pharm. Soc. Kor. v.37 Rho, Y. S.;Kang, H. S.;Sin, H. S.
  6. J. Am. Chem. Soc. v.103 Kimball, S. D.;Walt, D. R.;Johnson, F.
  7. J. Am. Chem. Soc. v.104 Sekizaki, H.;Jung, M.;McNamara, J. M.;Kishi, Y.
  8. J. Am. Chem. Soc. v.102 Arcamone, F.;Cassinelli, G.;DiMatteo, F.;Forenza, S.;Ripamonti, M. C.;Rivola, G.;Vigevani, A.
  9. Drugs Exp. Clin. Res. v.11 Tone, H.;Nishida, H.;Takeuchi, T.;Umezawa, H.
  10. J. Org. Chem. v.54 Hauser, F. M.;Hewawasam, P.;Rho, Y. S.
  11. J. Bull. Korean Chem. Soc. v.19 Rho, Y. S.;Kim, S. Y.;Cho, I. H.;Kang, H.-S.;Yoo, D. J.;Cheong, C. J.
  12. Bull. Korean Chem. Soc. v.17 Rho, Y. S.;Yoo, J. H.;Baek, B. N.;Kim, C. J.;Cho, I. H.
  13. J. Am. Chem. Soc. v.104 Boeckman, Jr. R. K.;Sum, F.-W.
  14. Tetrahedron v.40 Hauser, F. M.;Prasanna, S.
  15. J. Org. Chem. v.48 Hauser, F. M.;Prasanna, S.;Comb, D. W.
  16. Bull. Korean Chem. Soc. v.19 Rho, Y. S.;Park, S. H.;Kim, S. Y.;Cho, I. H.;Lee, C. H.;Kang, H.-S.;Cheong, C. J.
  17. Israel J. Chem. v.17 Olah, G. A.;Meider, D.
  18. Chem. Pharm. Bull. v.36 Tamura, Y.;Akai, S.;Kishimoto, H.;Sasho, M.;Kirihara, M.;Kita, Y.
  19. Tetrahedron v.52 Pasqui, F.;Canfarini, F.;Giolitti, A.;Guidi, A.;Pestellini, V.;Arcamone, F.
  20. J. Org. Chem. v.42 Smith, T. H.;Fujiwara, A. N.;Lee, W. W.;Wu, H. Y.;Henry, D. W.
  21. J. Org. Chem. v.46 Kende, A. S.;Boettger, S. D.
  22. Chem. Pharm. Bull. v.40 Kita, Y.;Maeda, H.;Kirihara, M.;Fujii, Y.;Nakajima, T.;Yamamoto, H.;Tamura, Y.;Fujoka, H.
  23. Tetrahedron Lett. v.33 Giolitt, A.;Guidi, A.;Pasqui, F.;Pestellini, V.;Arcamone, F.