A Route to Artificial Glycoconjugates and Oligosaccharides via Enzymatically Resolved Glycals: Dramatic Effects of the Handedness of the Sugar Domain Upon the Properties of an Anthracycline Drug

Journal of the American Chemical Society

Volumn 114, Issue 12, 1992, Pages 4518-4529

  Berkowitz, David B ^a,b   Danishefsky, Samuel J ^a,b   Schulte, Gayle K ^a,c  

^a YALE UNIVERSITY   (United States)

^b Center for Chemical Instrumentation ^*  (United States)

^c Department of Chemistry ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DAUNORUBICIN DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; X RAY ANALYSIS;

EID: 0026651052     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00038a011     Document Type: Article

References (64)

1. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235.
2. Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155-173.
3. Lemieux, R. U.; Morgan, A. R. Can. J. Chem. 1965, 43, 2190-2198.
4. Thiem, J.; Karl, H.; Schwentner, J. Synthesis 1978, 696-698.
5. Ramesh, S.; Kaila, N.; Grewal, G.; Franck, R. W. J. Org. Chem. 1990, 55, 5-7.
6. Halcomb, R. L.; Danishefsky, S. J. J. Org. Chem. 1989, 206, 6661-6666.
7. Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1990, 112, 5811-5819.
8. Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1991, 113, 5863-5864.
9. Gordon, D. M.; Danishefsky, S. J. Carbohydr. Res. 1990, 111, 361-366.
10. Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6656-6660.
11. Ferrier, R. J.; Prasad, N. J. Chem. Soc. C 1969, 570-575.
12. Ferrier, R. J. Adv. Carbohydr. Chem. Biochem. 1969, 24, 199.
13. Suzuki, K.; Friesen, R.; Sulikowski, G. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1990, 112, 8895-8902.
14. Halcomb, R. L.; Wittman, M. D.; Olson, S. H.; Danishefsky, S. J.; Golik, J.; Wong, H.; Vyas, D. J. Am. Chem. Soc. 1991, 113, 5080-5082.
15. Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 2, 273-289.
16. Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15-23.
17. Danishefsky, S. J. Aldrichimica Acta 1986, 19, 59-69.
18. Bednarski, M.; Danishefsky, S. J. J. Am. Chem. Soc. 1986, 108, 7060-7067.
19. Togni, A. Organometallics 1990, 9, 3106-3113.
20. Faller, J. W.; Smart, C. J. Tetrahedron Lett. 1989, 30, 1189-1192.
21. Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310-312.
22. Danishefsky, S. J.; Mating, C. J. J. Am. Chem. Soc. 1985, 107, 1269-1274.
23. Holla, E. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 220-221.
24. Hsu, S.-H.; Wu, S.-S.; Wang, Y.-F.; Wong, C.-H. Tetrahedron Lett. 1990, 31, 6403-6406.
25. Wang, Y.-F.; Chen, S.-T.; Liu, K. K. -C.; Wong, C.-H. Tetrahedron Lett. 1989, 30, 1917-1920.
26. Wang, Y.-F.; Wong, C.-H. J. Org. Chem. 1988, 53, 3127-3129.
27. Sweers, H. M.; Wong, C.-H. J. Am. Chem. Soc. 1986, 108, 6421-6422.
28. Berkowitz, D. B.; Danishefsky, S. J. Tetrahedron Lett. 1991, 32, 5497-5500.
29. Danishefsky, S. J.; Bednarski, M. Tetrahedron Lett. 1985, 26, 3411-3412.
30. Danishefsky, S. J.; Selnick, H. G.; Armistead, D. M.; Wincott, F. E. J. Am. Chem. Soc. 1987, 109, 8119-8120.
31. Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979-1981.
32. Micheel, F.; Klemer, A. Adv. Carbohydr. Chem. 1961, 16, 85-103.
33. Mukaiyama, T.; Murai, Y.; Shoda, S. Chem. Lett. 1981, 431-4321.
34. Mukaiyama, T.; Shoda, S. Chem. Lett. 1983, 935-938.
35. Szarek, W. A.; Grynkiewicz, G.; Doboszewski, B.; Hay, G. W. Chem. Lett. 1984, 1751-1754.
36. Nicolaou, K. C.; Dolle, R. E.; Papahatjis, D. P.; Randall, J. L. J. Am. Chem. Soc. 1984, 106, 4189-4192.
37. Hashimoto, S.; Hayashi, M.; Noyori, R. Tetrahedron Lett. 1984, 25, 1379-1382.
38. Thiem, J.; Wiesner, M. Synthesis 1988, 124-127.
39. Nicolaou, K. C.; Dolle, R. E.; Chucholowski, A.; Randall, J. L. J. Chem. Soc., Chem. Commun. 1984, 1153-1154.
40. Nicolaou, K. C.; Chucholowski, A.; Dolle, R. E.; Randall, J. L. J. Chem. Soc., Chem. Commun. 1984, 1155-1156.
41. Nicolaou, K. C.; Randall, J. L.; Furst, G. T. J. Am. Chem. Soc. 1985, 107, 5556-5558.
42. Kahne, D.; Walker, S.; Cheng, Y.; Van Engen, D. J. Am. Chem. Soc. 1989, 111, 6881-6882.
43. Crosswell, A. R. Personal communication (Bristol-Myers-Squibb, Wallingford, CT).
44. Roche, C. J.; Crothers, D. M.; Sulikowski, G. A.; Berkowitz, D. B.; Thomson, J. A.; Danishefsky, S. J. The Site Selectivity of Anthracycline Drugs, Book of Abstracts: Seventh Conversation in Biomolecular Stereodynamics, SUNY at Albany, June 18-23, 1991; Adenine Press: New York, 1991.
45. Horton, D.; Priebe, W.; Varella, O. Carbohydr. Res. 1985, 144, 305.
46. Neidle, S.; Taylor, G. Biochim. Biophys. Acta 1977, 450-459.
47. Anguili, R.; Foresti, E.; Riva Di Sanseverino, L.; Isaacs, N. W.; Kennard, O.; Motherwell, W. D. S.; Wampler, D. L.; Armacone, F. Nature (London), New Biol. 1971, 234, 78-80.
48. Von Dreele, R. B.; Einck, J. J. Acta Crystallogr. 1977, B33, 3283-3288.
49. Wang, A. H.-J.; Ughetto, G.; Quigley, G. J.; Rich, A. Biochemistry 1987, 26, 1152-1163.
50. Patel, D. J., Columbia University. Personal communication.
51. Danishefsky, S. J.; Kerwin, J. F., Jr.; Kobayashi, S. J. Am. Chem. Soc. 1982, 104, 358-360.
52. Sher, F.; Isidor, J. L.; Taneja, H. R.; Carlson, R. M. Tetrahedron Lett. 1977, 577-580.
53. Dale, J. A.; Lull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
54. Iselin, B.; Reichstein, T. Helv. Chim. Acta 1944, 27, 1200-1203.
55. Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G.; Hungate, R. J. Am. Chem. Soc. 1989, 111, 2967-2980.
56. Danishefsky, S. J.; DeNinno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082-2089.
57. Danishefsky, S. J.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803-3805.
58. Bartner, P.; Boxler, D. L.; Brambilla, R.; Mallams, A. K.; Morton, J. B.; Reichert, P.; Sancillo, F. D.; Surprenant, H.; Tomalesky, G.; Lukacs, G.; Olesker, A.; Thang, T. T.; Valente, L.; Omura, S. J. Chem. Soc., Perkin Trans. 1 1979, 1600-1624.
59. Blackburne, I. D.; Fredericks, P. M.; Guthrie, R. D. Aust. J. Chem. 1976, 29, 381.
60. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4156-4158.
61. Danishefsky, S. J.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360-362.
62. Matsumoto, T.; Tanaka, I.; Fukui, K. Bull. Chem. Soc. Jpn. 1971, 44, 3378-3382.
63. Jephcote, V. J.; Pratt, A. J.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1984, 800-802.
64. Danishefsky, S. J.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 1597-1598.