Total synthesis of 11-deoxydaunomycinone

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 7, 1982, Pages 421-423

  Gesson, Jean Pierre ^a   Mondon, Martine ^a  

^a Laboratoire de Chimie XII Synthèse et Réactivité de Produits Naturels ERA No 556 ^*  (France)

Author keywords

[No Author keywords available]

Indexed keywords

11 DEOXYDAUNOMYCINONE; DRUG ANALYSIS; DRUG IDENTIFICATION; DRUG SYNTHESIS; PRELIMINARY COMMUNICATION; THEORETICAL STUDY;

EID: 0020361985     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39820000421     Document Type: Article

References (22)

1. Presented in part at ESOC II, June 1981, Stresa, Italy
2. T. Oki, ‘Anthracyclines: Current Status and New Developments,’ eds. S. T. Crooke and S. D. Reich, Academic Press, 1980, ch. 19, p. 323
3. F. Arcamone, G. Cassinelli, F. Di Matteo, S. Forenza, M. C. Ripamonti, G. Rivola, A. Vigevani, J. Clardy, and T. McCabe, J. Am. Chem. Soc., 1980, 102, 1462
4. A. S. Kende and J. P. Rizzi, J. Am. Chem. Soc., 1981, 103, 4247
5. B. A. Pearlman, J. M. McNamara, I. Hasan, S. Matakeyama, M. Sekizaki, and Y. Kishi, J. Am. Chem. Soc., p. 4248
6. P. N. Confalone and G. Pizzolato, J. Am. Chem. Soc., p. 4251
7. Tsung-Tee Li and Yu Lin Wu, J. Am. Chem. Soc., p. 7007
8. S. D. Kimball, D. R. Walt, and F. Johnson, J. Am. Chem. Soc., 1981, 103, 1561
9. J. Yadav, P. Corey, Chi-Tung Hsu, K. Perlman, and C. J. Sih, Tetrahedron Lett., 1981, 811
10. A. S. Kende and S. D. Boettger, J. Org. Chem., 1981, 46, 2799
11. H. Umezawa, Y. Taka- hashi, M. Kinoshita, and H. Naganawa, J. Antibiot., 1980, 33, 1581
12. J. P. Gesson, J. C. Jacquesy, and M. Mondon, Tetrahedron Lett., 1980, 3351. The overall yield of (3) from Hagemann ester has been improved to about 50%. For alternative routes see
13. J. G. Bauman, R. B. Barber, R. D. Gless, and H. Rapoport, Tetrahedron Lett., 1980, 4777
14. J. Alexander, D. L. Flynn, L. A. Mitscher, and T. Veysoglu, Tetrahedron Lett., 1981, 3711
15. C. A. Brown and A. Yamaichi, J. Chem. Soc., Chem. Commun., 1979, 100
16. F. W. Sum and L. Weiler, Can. J. Chem., 1979, 57, 1431
17. R. H. Thomson, J. Org. Chem., 1948, 13, 377
18. R. L. Hannan, R. B. Barber, and H. Rapoport, J. Org. Chem., 1979, 44, 2153
19. J. N. Gardner, F. E. Carlon, and O. Gnoj, J. Org. Chem., 1968, 33, 3294
20. A. S. Kende, Y. Tsay, and J. E. Mills, J. Am. Chem. Soc., 1976, 98, 1969
21. T. H. Smith, A. N. Fujiwara, W. W. Lee, H. Y. Wu, and D. W. Henry, J. Org. Chem., 1977, 42, 3653
22. V. Carlo, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1977, 501