Synthesis of a highly functionalized γ-lactone as a precursor of 9- pentyl anthracyclines

Tetrahedron Asymmetry

Volumn 9, Issue 17, 1998, Pages 2999-3009

  Bertounesque, Emmanuel ^a   Millal, Fatima ^a   Meresse, Philippe ^a   Monneret, Claude ^a  

^a INSTITUT CURIE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3' MORPHOLINYL 9 PENTYLANTHRACYCLINE; ANTHRACYCLINE DERIVATIVE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER; CANCER CHEMOTHERAPY; DRUG SYNTHESIS; MULTIDRUG RESISTANCE; PRIORITY JOURNAL;

EID: 0032483443     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00320-6     Document Type: Article

References (47)

1. Arcamone, F. Doxorubicin; Academic Press: New York, 1981. Lown, J. W., Ed. Anthracycline and Anthracenedione Based Anticancer Agents; Elsevier: Amsterdam, 1988.
2. Arcamone, F. Doxorubicin; Academic Press: New York, 1981. Lown, J. W., Ed. Anthracycline and Anthracenedione Based Anticancer Agents; Elsevier: Amsterdam, 1988.
3. Endicott, J. A.; Ling, V. Annu. Rev. Biochem. 1989, 58, 137. Gottesman, M. M. Cancer Res. 1993, 53, 747.
4. Endicott, J. A.; Ling, V. Annu. Rev. Biochem. 1989, 58, 137. Gottesman, M. M. Cancer Res. 1993, 53, 747.
5. Suarato, A.; Angelucci, F.; Bargiotti, A.; Caruso, M.; Faiardi, D.; Capolongo, L.; Geroni, C.; Ripamonti, M.; Grandi, M. In Anthracycline Antibiotics; Priebe, W., Ed.; ACS Symposium Series 574; American Chemical Society: Washington, DC, 1995, p. 142.
6. Fachetti, I.; Grandi, M.; Cucchi, P.; Geroni, C.; Penco, S.; Vigevani, A. Anti-Cancer Drug Design 1991, 6, 385.
7. Coley, H. M.; Twentyman, P. R.; Workman, P. Anti-Cancer Drug Design 1992, 7, 471.
8. Coley, H. M.; Twentyman, P. R.; Workman, P. Eur. J. Cancer 1990, 26, 665.
9. Watanabe, M.; Komeshima, N.; Nakajima, S.; Tsuruo, T. Cancer Res. 1988, 48, 6653.
10. Bielack, S. S.; Kallenbach, K.; Looft, G.; Erttmann, R.; Winkler, K. Anticancer Res. 1995, 15, 1279. El-Zayat, A. A. E.; Izquierdo, M. A.; Clark, G. M.; Hoff, D. D. V. Invest. New Drugs 1995, 13, 125.
11. Bielack, S. S.; Kallenbach, K.; Looft, G.; Erttmann, R.; Winkler, K. Anticancer Res. 1995, 15, 1279. El-Zayat, A. A. E.; Izquierdo, M. A.; Clark, G. M.; Hoff, D. D. V. Invest. New Drugs 1995, 13, 125.
12. Westendorf, J.; Groth, G.; Steinheider, G.; Marquardt, H. J. Cell Biol. Toxicol. 1985, 1, 87. Westendorf, J.; Aydin, M.; Groth, G.; Weller, O.; Marquardt, H. Cancer Res. 1989, 49, 5262.
13. Westendorf, J.; Groth, G.; Steinheider, G.; Marquardt, H. J. Cell Biol. Toxicol. 1985, 1, 87. Westendorf, J.; Aydin, M.; Groth, G.; Weller, O.; Marquardt, H. Cancer Res. 1989, 49, 5262.
14. Monneret, C.; Florent, J.-C.; Gesson, J.-P.; Jacquesy, J.-C.; Tillequin, F.; Koch, M. In Anthracycline Antibiotics; Priebe, W., Ed.; ACS Symposium Series 574; American Chemical Society: Washington, DC, 1995, p. 78.
15. Nafziger, J.; Averland, G.; Bertounesque, E.; Gaudel, G.; Monneret, C. J. Antibiot. 1995, 48, 1185.
16. Monneret, C.; Florent, J.-C. Synlett 1994, 305.
17. For recent publications on the chemistry of the anthracycline antibiotics dealing with the construction of chiral tertiary hydroxy groups, see: Davis, F. A.; Clark, C.; Kumar, A.; Chen, B.-C. J. Org. Chem. 1994, 59, 1184. Cousson, A.; Le Gouadec, G.; Monneret, C.; Florent, J.-C. J. Chem. Soc., Chem. Commun. 1993, 388.
18. For recent publications on the chemistry of the anthracycline antibiotics dealing with the construction of chiral tertiary hydroxy groups, see: Davis, F. A.; Clark, C.; Kumar, A.; Chen, B.-C. J. Org. Chem. 1994, 59, 1184. Cousson, A.; Le Gouadec, G.; Monneret, C.; Florent, J.-C. J. Chem. Soc., Chem. Commun. 1993, 388.
19. 6, 80°C) gave the desired benzylidene acetal lactone 9 (60%). (Matrix presented)
20. Hanessian, S.; Plessas, N. R. J. Org. Chem. 1969, 34, 1035.
21. Hullar, T. L.; Siskin, S. B. J. Org. Chem. 1970, 35, 225.
22. Ishizumi, K.; Ohashi, N.; Tanno, N. J. Org. Chem. 1987, 52, 4477. Ishizumi, K.; Ohashi, N.; Tanno, N.; Sato, H.; Fukui, M.; Morisada, S. EP 107,486; US 4,673,668.
23. Ishizumi, K.; Ohashi, N.; Tanno, N. J. Org. Chem. 1987, 52, 4477. Ishizumi, K.; Ohashi, N.; Tanno, N.; Sato, H.; Fukui, M.; Morisada, S. EP 107,486; US 4,673,668.
24. Takahata, H.; Yamazaki, K.; Takamatsu, T.; Yamazaki, T.; Momose, T. J. Org. Chem. 1990, 55, 3947. Marfat, A.; McGuirk, P. R.; Kramer, R.; Helquist, P. J. Am. Chem. Soc. 1977, 99, 253.
25. Takahata, H.; Yamazaki, K.; Takamatsu, T.; Yamazaki, T.; Momose, T. J. Org. Chem. 1990, 55, 3947. Marfat, A.; McGuirk, P. R.; Kramer, R.; Helquist, P. J. Am. Chem. Soc. 1977, 99, 253.
26. Posner, G. H. Org. React. 1975, 22, 253.
27. For synthesis of epoxylactones, see: Adam, W.; Hadjiarapoglou, L.; Jäger, V.; Seidel, B. Tetrahedron Lett. 1989, 30, 4323. Lundt, I.; Pedersen, C. Synthesis 1992, 669.
28. For synthesis of epoxylactones, see: Adam, W.; Hadjiarapoglou, L.; Jäger, V.; Seidel, B. Tetrahedron Lett. 1989, 30, 4323. Lundt, I.; Pedersen, C. Synthesis 1992, 669.
29. Mitsunobu, O. Synthesis 1981, 1.
30. Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A.; Parker, D. J. Org. Chem. 1984, 49, 3928.
31. Alexakis, A.; Jachiet, D.; Normant, J.-F. Tetrahedron 1986, 42, 5607.
32. Lewis, R. G.; Gustafson, D. H.; Erman, W. F. Tetrahedron Lett. 1967, 401. Paquette, L. A.; Philips, J. C. Tetrahedron Lett. 1967, 4645. Anderson, P. H.; Stephenson, B.; Mosher, H. S. J. Am. Chem. Soc. 1974, 96, 3171.
33. Lewis, R. G.; Gustafson, D. H.; Erman, W. F. Tetrahedron Lett. 1967, 401. Paquette, L. A.; Philips, J. C. Tetrahedron Lett. 1967, 4645. Anderson, P. H.; Stephenson, B.; Mosher, H. S. J. Am. Chem. Soc. 1974, 96, 3171.
34. Lewis, R. G.; Gustafson, D. H.; Erman, W. F. Tetrahedron Lett. 1967, 401. Paquette, L. A.; Philips, J. C. Tetrahedron Lett. 1967, 4645. Anderson, P. H.; Stephenson, B.; Mosher, H. S. J. Am. Chem. Soc. 1974, 96, 3171.
35. Tomioka, K.; Cho Y.-S.; Sato, F.; Koga, K. J. Org. Chem. 1988, 53, 4094.
36. For example, see: Hine, J.; Brader Jr., W H. J. Am. Chem. Soc. 1953, 75, 3964. Bordwell, F. G.; Brannen Jr., W. T. J. Am. Chem. Soc. 1964, 86, 4645.
37. For example, see: Hine, J.; Brader Jr., W H. J. Am. Chem. Soc. 1953, 75, 3964. Bordwell, F. G.; Brannen Jr., W. T. J. Am. Chem. Soc. 1964, 86, 4645.
38. Florent, J.-C.; Ughetto-Monfrin, J.; Monneret, C. J. Org. Chem. 1987, 52, 1051.
39. Shibata, I.; Matsuo, F.; Baba, A.; Matsuda, H. J. Org. Chem. 1991, 56, 475.
40. Bennani, F.; Florent, J.-C.; Koch, M.; Monneret, C. Tetrahedron 1984, 40, 4665.
41. Genot, A.; Florent, J.-C.; Monneret, C. J. Org. Chem. 1987, 52, 1057.
42. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734.
43. Stork, G.; Cama, L. D.; Coulson, D. R. J. Am. Chem. Soc. 1974, 96, 5268. Stork, G.; Cohen, J. F. J. Am. Chem. Soc. 1974, 96, 5270. Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330.
44. Stork, G.; Cama, L. D.; Coulson, D. R. J. Am. Chem. Soc. 1974, 96, 5268. Stork, G.; Cohen, J. F. J. Am. Chem. Soc. 1974, 96, 5270. Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330.
45. Stork, G.; Cama, L. D.; Coulson, D. R. J. Am. Chem. Soc. 1974, 96, 5268. Stork, G.; Cohen, J. F. J. Am. Chem. Soc. 1974, 96, 5270. Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330.
46. Molecular mechanics calculations (Chem 3D Pro, MM2 force field) find the following conformation related to 23: (Matrix presented)
47. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.