Synthetic progress in saframycins and ecteinascidins

Chinese Journal of Organic Chemistry

Volumn 25, Issue 1, 2005, Pages 42-52

  Wang, Ye ^a   Tang, Ye Feng ^a   Liu, Zhan Zhu ^a   Chen, Shi Zhi ^a   Liang, Xiao Tian ^a  

^a INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Bis tetrahydroisoquinoline alkaloid; Ecteinascidin; Phthalascidin; Saframycin; Synthesis

Indexed keywords

ALKALOID DERIVATIVE; ANTINEOPLASTIC ANTIBIOTIC; PHTHALASCIDIN; SAFRAMYCIN A; SAFRAMYCIN B; TETRAHYDROISOQUINOLINE DERIVATIVE; TRABECTEDIN; UNCLASSIFIED DRUG;

BIOSYNTHESIS; DRUG MECHANISM; DRUG SYNTHESIS; REACTION ANALYSIS; REVIEW; STRUCTURE ANALYSIS; TECHNIQUE;

EID: 15744362103     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (67)

1. For a review see: Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669.
2. (a) Arai, T.; Takahashi, K.; Kubo, A. J. Antibiot 1977, 30, 1015.
3. (b) Arai, T.; Takahashi, K.; Kubo, A.; Nakahara, S. Experientia 1980, 36, 1025.
4. (a) Wright, A. E.; Forleo, D. A.; Gunawardana, G. P.; Gunasekera, S. P.; Koehn, F. E.; McConnell, O. J. J. Org. Chem. 1990, 55, 4508.
5. (b) Rinehart, K. L.; Holt, T. G.; Fregeau, N. L.; Stroh, J. G.; Kieffer, P. A.; Sun, F.; Li, L. H.; Martin, D. G. J. Org. Chem. 1990, 55, 4512.
6. (c) Rinehart, K. L.; Holt, T. G.; Fregeau, N. L.; Kieffer, P. A.; Wilson, G. R.; Perun, T. J.; Sakai, R.; Thompson, A. G.; Stroh, J. G.; Shield, L. S.; Seigler, D. S. J. Nat. Prod. 1990, 53, 771.
7. (d) Rinehart, K. L.; Holt, T. G.; Fregeau, N. L.; Stroh, J. G.; Kieffer, P. A.; Sun, F.; Li, L. H.; Martin, D. G. J. Org. Chem. 1991, 56, 1676.
8. (e) Guan, Y.; Sakai, R.; Rinehart, K. L.; Wang, A. H.-J. J. Biomol. Struct. Dyn. 1993, 10, 793.
9. Mikami, Y.; Takahashi, K.; Arai, T.; Namikoshi, M.; Iwasaki, S.; Okuda, S. J. Biol. Chem. 1985, 260, 344.
10. Arai, T.; Yazawa, K.; Takahashi, K.; Maeda, A.; Mikami, Y. Antimicrob. Agents Chemother. 1985, 28, 5.
11. Mikami, Y.; Yokoyama, K.; Tabeta, H.; Nakagaki, K.; Arai, T. J. Pharmacobio. Dyn. 1981, 4, 282.
12. Asaoka, T.; Yazawa, K.; Mikami, Y.; Arai, T.; Takahashi, K. J. Antibiot. 1982, 35, 1708.
13. Arai, T.; Takahashi, K.; Ishiguro, K.; Yazawa, K. J. Antibiot. 1980, 33, 951.
14. Lown, J. W.; Joshua, A. V.; Lee, J. S. Biochemistry 1982, 21, 419.
15. Hill, G. C.; Remers, W. A. J. Med. Chem. 1991, 34, 1990.
16. Fukuyama, T.; Sachleben, R. A. J. Am. Chem. Soc. 1982, 104, 4957.
17. (a) Kubo, A.; Saito, N.; Yamauchi, R.; Sakai, S. Chem. Pharm. Bull. 1987, 35, 2158.
18. (b) Kubo, A.; Saito, N.; Yamato, H.; Kawakami, Y. Chem. Pharm. Bull 1987, 35, 2525.
19. (c) Kubo, A.; Saito, N.; Nakamura, M.; Ogata, K.; Sakai, S. Heterocycles 1987, 26, 1765.
20. (d) Kubo, A.; Saito, N.; Yamato, H.; Yamauchi, R.; Hiruma, K.; Inoue, S. Chem. Pharm. Bull. 1988, 36, 2607.
21. (e) Kubo, A.; Saito, N.; Yamato, H.; Masubuchi, K.; Nakamura, M. J. Org. Chem. 1988, 53, 4295.
22. Fukuyama, T.; Yang, L.; Ajeck, K. L.; Sachleben, R. A. J. Am. Chem. Soc. 1990, 112, 3712.
23. Saito, N.; Yamauchi, R.; Nishioka, H.; Ida, S.; Kubo, A. J. Org. Chem. 1989, 54, 5391.
24. Saito, N.; Tanitsu, M.; Betsui, T.; Suzuki, R.; Kubo, A. Chem. Pharm. Bull. 1997, 45, 1120.
25. (a) Saito, N.; Obara, Y.; Azumaya, M.; Kubo, A. Chem. Pharm. Bull. 1992, 40, 2620.
26. (b) Aaito, N.; Obara, Y.; Aihara, T.; Harada, S.; Shida, Y.; Kubo, A. Tetrahedron 1994, 50, 3915.
27. Fukuyama, T.; Linton, S. D.; Tun, M. M. Tetrahedron Lett. 1990, 31, 5989.
28. (a) Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828.
29. (b) Myers, A. G.; Schnider, P.; Kwon, S.; Kung, D. W. J. Org. Chem. 1999, 64, 3322.
30. (c) Myers, A. G.; Kung, D. W.; Zhong, B.; Movassaghi, M.; Kwon, S. J. Am. Chem. Soc. 1999, 121, 8401.
31. Myers, A. G.; Kung, D. W. Org. Lett. 2000, 2, 3019.
32. Myers, A. G.; Plowright, A. T. J. Am. Chem. Soc. 2001, 123, 5114.
33. Myers, A. G.; Lanman, B. A. J. Am. Chem. Soc. 2002, 124, 12969.
34. (a) Kurihara, H.; Mishima, H. Tetrahedron Lett. 1982, 23, 3639.
35. (b) Kurihara, H.; Mishima, H. Heterocycles 1982, 17, 191.
36. (c) Kurihara, H.; Mishima, H.; Arai, M. Heterocycles 1986, 24, 1549.
37. Ong, C. W.; Lee, H. C. Aust. J. Chem. 1990, 43, 773.
38. Shawe, T. T.; Liebeskind, L. S. Tetrahedron 1991, 47, 5643.
39. Kubo, A.; Nakai, T.; Koizumi, Y.; Saito, N.; Mikami, Y.; Yazawa, K.; Uno, J. Heterocycles 1992, 34, 1201.
40. Kubo, A.; Nakai, T.; Koizumi, Y.; Kitahara, Y.; Saito, N.; Mikami, Y.; Yazawa, K.; Uno, J. Heterocycles 1996, 42, 195.
41. Saito, N.; Harada, S.; Inouye, I.; Yamaguchi, K.; Kubo, A. Tetrahedron 1995, 51, 8231.
42. Jeedigunta, S.; Krenisky, J. M.; Ker, R. G. Tetrahedron 2000, 56, 3303.
43. Sakai, R.; Jares-Erijman, E. A.; Manzanares, I.; Elipe, M. V. S.; Rinehart, K. L. J. Am. Chem. Soc. 1996, 118, 9017.
44. Pommier, Y.; Kohlhagen, G.; Bailly, C.; Waring, M.; Mazumder, A.; Kohn, K. W. Biochemistry 1996, 35, 13303.
45. (a) Moore, B. M., II; Seaman, F. C.; Hurley, L. H. J. Am. Chem. Soc. 1997, 119, 5475.
46. (b) Moore, R. M., II; Seaman, F. C.; Wheelhouse, R. T.; Hurley, L. H. J. Am. Chem. Soc. 1998, 120, 2490.
47. (c) Erratum: Moore, R. M., II; Seaman, F. C.; Wheelhouse, R. T.; Hurley, L. H. J. Am. Chem. Soc. 1998, 120, 9973.
48. (d) Seaman, F. C.; Hurley, L. H. J. Am. Chem. Soc. 1998, 120, 13028.
49. (e) Zewail-Foote, M.; Hurley, L. H. J. Med. Chem. 1999, 42, 2493.
50. Zewail-Foote, M.; Hurley, L. H. J. Am. Chem. Soc. 2001, 123, 6485.
51. For clinical data see: (a) Ryan, D. P.; Supko, J. G.; Eder, J. P.; Seiden, M. V.; Demetri, G.; Lynch, T. J.; Fischman, A. J.; Davis, J.; Jimeno, J.; Clark, J. W. Clin. Cancer Res. 2001, 7, 231. (b) Zelek, L.; Yovine, A.; Etienne, B.; Jimeno, J.; Taamma, A.; Martin, C.; Spielmann, M.; Cvitkovic, E.; Misset, J. L. The American Society of Clinical Oncology, 36th Annual Meeting, New Orleans, May 20-23, 2000, Abstract number 592. (c) Delaloge, S.; Yovine, A.; Taamma, A.; Cottu, P.; Riofrio, M.; Raymond, E.; Brain, E.; Marty, M.; Jimeno, J.; Cvitkovic, E.; Misset, J. L. The American Society of Clinical Oncology, 36th Annual Meeting, New Orleans, May 20-23, 2000, Abstract number 2181. (d) Le Cesne, A.; Judson, I.; Blay, J. Y.; Radford, J.; an Oosterom, A.; Lorigan, P.; Rodenhuis, E.; Donato Di Paoula, E.; Van Glabbeke, M.; Jimeno, J.; Verweij, J. The American Society of Clinical Oncology, 36th Annual Meeting, New Orleans, May 20-23, 2000, Abstract number 2182. (e) Aune, G. J.; Furuta, T.; Pommier, Y. Anti-Cancer Drugs 2002, 13, 545.
52. For clinical data see: (a) Ryan, D. P.; Supko, J. G.; Eder, J. P.; Seiden, M. V.; Demetri, G.; Lynch, T. J.; Fischman, A. J.; Davis, J.; Jimeno, J.; Clark, J. W. Clin. Cancer Res. 2001, 7, 231. (b) Zelek, L.; Yovine, A.; Etienne, B.; Jimeno, J.; Taamma, A.; Martin, C.; Spielmann, M.; Cvitkovic, E.; Misset, J. L. The American Society of Clinical Oncology, 36th Annual Meeting, New Orleans, May 20-23, 2000, Abstract number 592. (c) Delaloge, S.; Yovine, A.; Taamma, A.; Cottu, P.; Riofrio, M.; Raymond, E.; Brain, E.; Marty, M.; Jimeno, J.; Cvitkovic, E.; Misset, J. L. The American Society of Clinical Oncology, 36th Annual Meeting, New Orleans, May 20-23, 2000, Abstract number 2181. (d) Le Cesne, A.; Judson, I.; Blay, J. Y.; Radford, J.; an Oosterom, A.; Lorigan, P.; Rodenhuis, E.; Donato Di Paoula, E.; Van Glabbeke, M.; Jimeno, J.; Verweij, J. The American Society of Clinical Oncology, 36th Annual Meeting, New Orleans, May 20-23, 2000, Abstract number 2182. (e) Aune, G. J.; Furuta, T.; Pommier, Y. Anti-Cancer Drugs 2002, 13, 545.
53. For clinical data see: (a) Ryan, D. P.; Supko, J. G.; Eder, J. P.; Seiden, M. V.; Demetri, G.; Lynch, T. J.; Fischman, A. J.; Davis, J.; Jimeno, J.; Clark, J. W. Clin. Cancer Res. 2001, 7, 231. (b) Zelek, L.; Yovine, A.; Etienne, B.; Jimeno, J.; Taamma, A.; Martin, C.; Spielmann, M.; Cvitkovic, E.; Misset, J. L. The American Society of Clinical Oncology, 36th Annual Meeting, New Orleans, May 20-23, 2000, Abstract number 592. (c) Delaloge, S.; Yovine, A.; Taamma, A.; Cottu, P.; Riofrio, M.; Raymond, E.; Brain, E.; Marty, M.; Jimeno, J.; Cvitkovic, E.; Misset, J. L. The American Society of Clinical Oncology, 36th Annual Meeting, New Orleans, May 20-23, 2000, Abstract number 2181. (d) Le Cesne, A.; Judson, I.; Blay, J. Y.; Radford, J.; an Oosterom, A.; Lorigan, P.; Rodenhuis, E.; Donato Di Paoula, E.; Van Glabbeke, M.; Jimeno, J.; Verweij, J. The American Society of Clinical Oncology, 36th Annual Meeting, New Orleans, May 20-23, 2000, Abstract number 2182. (e) Aune, G. J.; Furuta, T.; Pommier, Y. Anti-Cancer Drugs 2002, 13, 545.
54. For clinical data see: (a) Ryan, D. P.; Supko, J. G.; Eder, J. P.; Seiden, M. V.; Demetri, G.; Lynch, T. J.; Fischman, A. J.; Davis, J.; Jimeno, J.; Clark, J. W. Clin. Cancer Res. 2001, 7, 231. (b) Zelek, L.; Yovine, A.; Etienne, B.; Jimeno, J.; Taamma, A.; Martin, C.; Spielmann, M.; Cvitkovic, E.; Misset, J. L. The American Society of Clinical Oncology, 36th Annual Meeting, New Orleans, May 20-23, 2000, Abstract number 592. (c) Delaloge, S.; Yovine, A.; Taamma, A.; Cottu, P.; Riofrio, M.; Raymond, E.; Brain, E.; Marty, M.; Jimeno, J.; Cvitkovic, E.; Misset, J. L. The American Society of Clinical Oncology, 36th Annual Meeting, New Orleans, May 20-23, 2000, Abstract number 2181. (d) Le Cesne, A.; Judson, I.; Blay, J. Y.; Radford, J.; an Oosterom, A.; Lorigan, P.; Rodenhuis, E.; Donato Di Paoula, E.; Van Glabbeke, M.; Jimeno, J.; Verweij, J. The American Society of Clinical Oncology, 36th Annual Meeting, New Orleans, May 20-23, 2000, Abstract number 2182. (e) Aune, G. J.; Furuta, T.; Pommier, Y. Anti-Cancer Drugs 2002, 13, 545.
55. For clinical data see: (a) Ryan, D. P.; Supko, J. G.; Eder, J. P.; Seiden, M. V.; Demetri, G.; Lynch, T. J.; Fischman, A. J.; Davis, J.; Jimeno, J.; Clark, J. W. Clin. Cancer Res. 2001, 7, 231. (b) Zelek, L.; Yovine, A.; Etienne, B.; Jimeno, J.; Taamma, A.; Martin, C.; Spielmann, M.; Cvitkovic, E.; Misset, J. L. The American Society of Clinical Oncology, 36th Annual Meeting, New Orleans, May 20-23, 2000, Abstract number 592. (c) Delaloge, S.; Yovine, A.; Taamma, A.; Cottu, P.; Riofrio, M.; Raymond, E.; Brain, E.; Marty, M.; Jimeno, J.; Cvitkovic, E.; Misset, J. L. The American Society of Clinical Oncology, 36th Annual Meeting, New Orleans, May 20-23, 2000, Abstract number 2181. (d) Le Cesne, A.; Judson, I.; Blay, J. Y.; Radford, J.; an Oosterom, A.; Lorigan, P.; Rodenhuis, E.; Donato Di Paoula, E.; Van Glabbeke, M.; Jimeno, J.; Verweij, J. The American Society of Clinical Oncology, 36th Annual Meeting, New Orleans, May 20-23, 2000, Abstract number 2182. (e) Aune, G. J.; Furuta, T.; Pommier, Y. Anti-Cancer Drugs 2002, 13, 545.
56. Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 9202.
57. Martinez, E. J.; Corey, E. J. Org. Lett. 1999, 1, 75.
58. Cuevas, C.; Pérez, M; Martín, M. J.; Chicharro, J. L.; Fernádez-Rivas, C.; Glores, M.; Francesch, A.; Gallego, P.; Zarzuelo, M.; de la Calle, F.; García, J.; Polanco, C.; Rodríguez, I.; Manzanares, I. Org. Lett. 2000, 2, 2545.
59. Menchaca, R.; Martínez, V.; Rodríguez, A.; Rodríguez, N.; Flores, M.; Gallego, P.; Manzanares, I.; Cuevas, C. J. Org. Chem. 2003, 68, 8859.
60. Endo, A.; Yanagisawa, A.; Abe, M.; Tohma, S.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 6552.
61. Martinez, E. J.; Owa, T.; Schreiber, S. L.; Corey, E. J. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 3496.
62. Martinez, E. J.; Corey, E. J. Org. Lett. 2000, 2, 993.
63. (a) Zhou, B.; Edmondson, S.; Padron, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2039.
64. (b) Zhou, B.; Guo, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2043.
65. Herberich, B.; Kinugawa, M.; Vazquez, A.; Williams, R. M. Tetrahedron Lett. 2001, 42, 543.
66. Jin, W.; Metobo, S.; Williams, R. M. Org. Lett. 2003, 5, 2095.
67. Tang, Y. F.; Liu, Z. Z.; Chen, S. Z. Tetrahedron Lett. 2003, 44, 7091.