OSW Saponins: Facile synthesis toward a new type of structures with potent antitumor activities

Journal of Organic Chemistry

Volumn 70, Issue 25, 2005, Pages 10354-10367

  Shi, Bingfeng ^a   Tang, Pingping ^a   Hu, Xiaoyi ^b   Liu, Jun O ^b   Yu, Biao ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERS; HYDROXYLATION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ANTITUMOR ACTIVITIES; CROSS METHTHESIS (CM) REACTIONS; OSW SAPONINS; STEREOSELECTIVITY; STRUCTURE-ACTIVITY RELATIONSHIPS (SAE);

AROMATIC COMPOUNDS;

ALLYL COMPOUND; ANTINEOPLASTIC AGENT; ESTER DERIVATIVE; HYDROXYL GROUP; KETONE DERIVATIVE; LACTONE DERIVATIVE; PRASTERONE; PROPIONIC ACID DERIVATIVE; PYRAN DERIVATIVE; SAPONIN DERIVATIVE;

ACYLATION; ALDOL REACTION; AMINOLYSIS; ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG MECHANISM; DRUG POTENCY; DRUG SYNTHESIS; FEASIBILITY STUDY; HUMAN; HUMAN CELL; LILY; NONHUMAN; QUANTUM YIELD; REACTION ANALYSIS; RING CLOSING METATHESIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CHOLESTENONES; DEHYDROEPIANDROSTERONE; HUMANS; SAPONINS; STEREOISOMERISM;

EID: 28744456358     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051536b     Document Type: Article

References (65)

1. Kubo, S.; Mimaki, Y.; Terao, M.; Sashida, Y.; Nikaido, T.; Ohmoto, T. Phytochemistry 1992, 31, 3969.
2. (a) Mimaki, Y.; Kuroda, M.; Kameyama, A.; Sashida, Y.; Hirano, T.; Oka, K.; Maekawa, R.; Wada, T.; Sugita, K.; Beutler, J. A. Bioorg. Med. Chem. Lett. 1997, 7, 633.
3. (b) Rouhi, A. M. Chem. Eng. News 1995, September 11, 28.
4. 50 values of OSW-1 against the NCI 60 cell-line tumor panel, see the Supporting Information in ref 4c.
5. (a) Kuroda, M.; Mimaki, Y.; Yokosuka, A.; Hasegawa, F.; Sashida, Y. J. Nat. Prod. 2002, 65, 1417.
6. (b) Kuroda, M.; Mimaki, Y.; Yokosuka, A.; Sashida, Y. Chem. Pharm. Bull. 2001, 49, 1042.
7. (c) Kuroda, M.; Mimaki, Y.; Yokosuka, A.; Sashida, Y.; Beutler, J. A. J. Nat. Prod. 2001, 64, 88.
8. Guo, C.; Fuchs, P. L. Tetrahedron Lett. 1998, 39, 1099.
9. Deng, S.; Yu, B.; Lou, Y.; Hui, Y. J. Org. Chem. 1999, 64, 202.
10. (a) Yu, W.; Jin, Z. J. Am. Chem. Soc. 2001, 123, 3369.
11. (b) Yu, W.; Jin, Z. J. Am. Chem. Soc. 2002, 124, 6576.
12. (a) Morzycki, J. W.; Gryszkiewicz, A.; Jastrzebska, I. Tetrahedron Lett. 2000, 41, 3751.
13. (b) Morzycki, J. W.; Wojtkielewicz, A. Carbohydr. Res. 2002, 337, 1269.
14. For other efforts toward the synthesis of OSW saponins, see (a) Morzycki, J. W.; Gryszkiewicz, A. Pol. J. Chem. 2001, 75, 983.
15. (b) Morzycki, J. W.; Gryszkiewicz, A. Jastrzebska, I. Tetrahedron 2001, 57, 2185.
16. (c) Morzycki, J. W.; Wojtkielewicz, A.; Gryszkiewicz, A.; Wolczynski, S. Bioorg. Med. Chem. Lett. 2004, 14, 3323.
17. (d) Xu, Q.; Peng, X.; Tian, W. Tetrahedron Lett. 2003, 44, 9375.
18. Guo, C.; LaCour, T. G.; Fuchs, P. L. Bioorg. Med. Chem. Lett. 1999, 9, 419.
19. (a) Ma, X.; Yu, B.; Hui, Y.; Miao, Z.; Ding, J. Carbohydr. Res. 2000, 329, 495.
20. (b) Ma, X.; Yu, B.; Hui, Y.; Miao, Z.; Ding, J. Carbohydr. Res. 2001, 334, 159.
21. Ma, X.; Yu, B.; Hui, Y.; Miao, Z.; Ding, J. Bioorg. Med. Chem. Lett. 2001, 11, 2153.
22. Deng, L.; Wu, H.; Yu, B.; Jiang, M.; Wu, J. Chin. J. Chem. 2004, 22, 994.
23. Deng, L.; Wu, H.; Yu, B.; Jiang, M.; Wu, J. Bioorg. Med. Chem. Lett. 2004, 14, 2781.
24. Shi, B.; Wu, H.; Yu, B.; Wu, J. Angew. Chem., Int. Ed. 2004, 43, 4324.
25. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556.
26. (a) Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920.
27. (b) Kleschick, W. A.; Buse, C. T.; Heathcock, C. H. J. Am. Chem. Soc. 1977, 99, 247.
28. (c) Evans, D. A. Top. Stereochem. 1982, 13, 1.
29. Mazur, Y.; Danieli, N.; Sondheimer, F. J. Am. Chem. Soc. 1960, 82, 5889.
30. Doller, D.; Gros, E. G. Synth. Commun. 1990, 20, 3115.
31. Numazawa, M.; Nagaoka, M.; Osawa, Y. J. Org. Chem. 1982, 47, 4024.
32. (a) Ireland, R. E.; Mueller, R. H. J. Am. Chem. Soc. 1976, 98, 2891.
33. (b) Ireland, R. E.; Wipf, P.; Armstrong, J. D., III J. Org. Chem. 1991, 56, 650.
34. (c) Oare, D. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 157.
35. Corey, E. J.; Gross, A. W. Tetrahedron Lett. 1984, 25, 495.
36. Grigsby, W. E.; Hind, J.; Chanley, J.; Westheimer, F. H. J. Am. Chem. Soc. 1942, 64, 2606.
37. Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, FL, 1984; Vol. 3, p 111 and references therein.
38. Otera, J.; Fujita, Y.; Fukuzumi, S. Synlett 1994, 213.
39. (a) Oka, K.; Hara, S. J. Org. Chem. 1978, 43, 4408.
40. (b) Lardon, A.; Reichstein, T. Helv. Chim. Acta 1941, 24, 1127.
41. (c) Hey, D. H.; Honeyman, J.; Peal, W. J. J. Chem. Soc. 1954, 185, 2648.
42. (a) Marino, J. P.; Abe, H. J. Am. Chem. Soc. 1981, 103, 2907.
43. (b) Schmuff, N. R.; Trost, B. M. J. Org. Chem. 1983, 48, 1404.
44. (a) Piatak, D. M.; Wicha, J. Chem. Rev. 1978, 78, 199.
45. (b) Ibuka, T.; Taga, T. J. Org. Chem. 1988, 53, 3947.
46. (c) Nes, W. R.; Varkey, T. E.; Krevitz, K. J. Am. Chem. Soc. 1977, 99, 260.
47. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
48. (a) Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 18, 4171.
49. (b) Levin, J. I.; Turos, E.; Weinreb, S. M. Synth. Commun. 1982, 12, 989.
50. Shimizu, T.; Osako, K.; Nakata, T. Tetrahedron Lett. 1997, 38, 2685.
51. Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G. Dolling, U.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461.
52. Graham, S. L.; Scholz, T. H. Tetrahedron Lett. 1990, 31, 6269.
53. (a) Sibi, M. P.; Sharma, R.; Paulson, K. L. Tetrahedron Lett. 1992, 33, 1941.
54. (b) Sibi, M. P.; Marvin, M.; Sharma, R. J. Org. Chem. 1995, 60, 5016.
55. Schlosser, M.; Strunk, S. Tetrahedron Lett. 1984, 25, 741.
56. Paquette, L. A.; Wang, H.; Zhao, M. J. Am. Chem. Soc. 1998, 120, 5213.
57. (a) Wada, T.; Ohkubo, A.; Mochizuki, A.; Sekine, M. Tetrahedron Lett. 2001, 42, 1069.
58. (b) Love, K. R.; Andrade, R. B.; Seeberger, P. H. J. Org. Chem. 2001, 66, 8165.
59. Huang, P.; Zheng, X.; Deng, X. Tetrahedron Lett. 2001, 42, 9039.
60. For a recent review on cross metathesis, see Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
61. Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58.
62. Chatterjee, A. K.; Choi, T. L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
63. For the X-ray diffraction analysis data, see Supporting Information.
64. Zhang, Y.; Griffith, E. C.; Sage, J.; Jacks, T.; Liu, J. O. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 6427.
65. For compounds not been described in this section, see Supporting Information.