Synthesis of 11-deoxydaunomycinone and novel 10-fluoroanthracyclinone derivatives

Bulletin of the Korean Chemical Society

Volumn 20, Issue 5, 1999, Pages 551-555

  Rho, Young S ^c   Choi, Younghee ^c   Kim, Gyuil ^c   Sin, Hongsig ^c   Yoo, Dong Jin ^a   Kim, Sun Ha ^b   Cheong, Chaejoon ^c  

^a Seonam University   (South Korea)

^b Korea Basic Science Institute (KBSI)   (South Korea)

^c Chonbuk National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

11 DEOXYDAUNOMYCINONE; ANTHRACYCLINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; EPOXIDATION; FLUORINATION; HYDROLYSIS; OXIDATION REDUCTION REACTION; SYNTHESIS;

EID: 0033587179     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (23)

1. (a) Arcamone, F. Doxorubicin; Academic press: New York, 1981.
2. (b) Priebe, W. Anthracycline Antibiotics; ACS Symposium Series 574, 1995.
3. Kelly, T. R. Recent Aspects of Anthracyclinone Chemistry; Tetrahedron Symposia-in Print No. 17, Pergamon press: 1984.
4. Wong, C. M.; Schwenk, R.; Popein, D.; Ho, T. L. Can. J. Chem. 1973, 51, 466.
5. (a) Rho, Y. S.; Kang, H. S.; Sin, H. S. J. Pharm. Soc. Kor. 1993, 37, 555.
6. (b) Kimball, S. D.; Walt, D. R.; Johnson, F. J. Am. Chem. Soc. 1981, 103, 1561.
7. (c) Sekizaki, H.; Jung, M.; McNamara, J. M.; Kishi, Y. J. Am. Chem. Soc. 1982, 104. 7372.
8. Arcamone, F.; Cassinelli, G.; DiMatteo, F.; Forenza, S.; Ripamonti, M. C.; Rivola, G.; Vigevani, A. J. Am. Chem. Soc. 1980, 102, 1462.
9. Tone, H.; Nishida, H.; Takeuchi, T.; Umezawa, H. Drugs Exp. Clin. Res. 1985, 11, 9.
10. (a) Hauser, F. M.; Hewawasam, P.; Rho, Y. S. J. Org. Chem. 1989, 54, 5110.
11. (b) Rho, Y. S.; Kim, S. Y.; Cho, I. H.; Kang, H.-S.; Yoo, D. J.; Cheong, C. J. Bull. Korean Chem. Soc. 1998, 19, 1059.
12. Rho, Y. S.; Yoo, J. H.; Baek, B. N.; Kim, C. J.; Cho, I. H. Bull. Korean Chem. Soc. 1996, 17, 946.
13. Boeckman, Jr. R. K.; Sum, F.-W. J. Am. Chem. Soc. 1982, 104, 4604.
14. Hauser, F. M.; Prasanna, S. Tetrahedron 1984, 40, 4711.
15. Hauser, F. M.; Prasanna, S.; Comb, D. W. J. Org. Chem. 1983, 48, 1328.
16. Rho, Y. S.; Park, S. H.; Kim, S. Y.; Cho, I. H.; Lee, C. H.; Kang, H.-S.; Cheong, C. J. Bull. Korean Chem. Soc. 1998, 19, 74.
17. Olah, G. A.; Meider, D. Israel J. Chem. 1978, 17, 148.
18. Tamura, Y.; Akai, S.; Kishimoto, H.; Sasho, M.; Kirihara, M.; Kita, Y. Chem. Pharm. Bull. 1988, 36, 3897.
19. Pasqui, F.; Canfarini, F.; Giolitti, A.; Guidi, A.; Pestellini, V.; Arcamone, F. Tetrahedron 1996, 52, 185.
20. (a) Smith, T. H.; Fujiwara, A. N.; Lee, W. W.; Wu, H. Y.; Henry, D. W. J. Org. Chem. 1977, 42, 3653.
21. (b) Kende, A. S.; Boettger, S. D. J. Org. Chem. 1981, 46, 2799.
22. Kita, Y.; Maeda, H.; Kirihara, M.; Fujii, Y.; Nakajima, T.; Yamamoto, H.; Tamura, Y.; Fujoka, H. Chem. Pharm. Bull. 1992, 40, 61.
23. Giolitt, A.; Guidi, A.; Pasqui, F.; Pestellini, V.; Arcamone, F. Tetrahedron Lett. 1992, 33, 1637.