Asymmetric total syntheses of ecteinascidin 597 and ecteinascidin 583

Angewandte Chemie - International Edition

Volumn 45, Issue 47, 2006, Pages 8028-8032

  Chen, Jinchun ^a   Chen, Xiaochuan ^a   Willot, Matthieu ^a   Zhu, Jieping ^a  

^a CNRS   (France)

Author keywords

Alkaloids; Antitumor agents; Asymmetric synthesis; Marine natural products; Pictet Spengler reaction

Indexed keywords

PROBLEM SOLVING; SYNTHESIS (CHEMICAL);

ALKALOIDS; ANTITUMOR AGENTS; ASYMMETRIC SYNTHESIS; MARINE NATURAL PRODUCTS; PICTET SPENGLER REACTION; STEREOSELECTIVE;

BIOLOGICAL MATERIALS;

ALKYLATING AGENT; BIOLOGICAL PRODUCT; ECTEINASCIDIN 583; ECTEINASCIDIN 597; ISOQUINOLINE DERIVATIVE;

ANIMAL; ARTICLE; BIOLOGY; CHEMICAL MODEL; STEREOISOMERISM; SYNTHESIS;

ANIMALS; ANTINEOPLASTIC AGENTS, ALKYLATING; BIOLOGICAL PRODUCTS; ISOQUINOLINES; MARINE BIOLOGY; MODELS, CHEMICAL; STEREOISOMERISM;

EID: 33845476049     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603179     Document Type: Article

References (58)

1. a) A. E. Wright, D. A. Forleo, G. P. Gunawardana, S. P. Gunasekera, F. E. Koehn, O. J. McConnell, J. Org. Chem. 1990, 55, 4508-4512;
2. b) K. L. Rinehart, T. G. Holt, N. L. Fregeau, J. G. Stroh, P. A. Keifer, F. Sun, L. H. Li, D. G. Martin, J. Org. Chem. 1990, 55, 4512-4515;
3. c) R. Sakai, K. L. Rinehart, Y. Guan, A. H. J. Wang, Proc. Natl. Acad. Sci. USA 1992, 89, 11456-11460;
4. d) R. Sakai, E. A. Jares-Erijman, I. Manzanares, M. V. S. Elipe, K. L. Rinehart, J. Am. Chem. Soc. 1996, 118, 9017-9023;
5. e) K. Suwanborirux, K. Charupant, S. Amnuoypol, S. Pummangura, A. Kubo, N. Saito, J. Nat. Prod. 2002,65, 935-937.
6. K. L. Rinehart, Med. Drug. Rev. 2000, 1-27.
7. J. D. Scott, R. M. Williams, Chem. Rev. 2002, 102, 1669-1730.
8. a) E. J. Corey, D. Y. Gin, R. S. Kania, J. Am. Chem. Soc. 1996, 118, 9202-9203;
9. b) E. J. Martinez, E. J. Corey, Org. Lett. 2000, 2, 993-996.
10. a) A. Endo, A. Yanagisawa, M. Abe, S. Tohma, T. Kan, T. Fukuyama, J. Am. Chem. Soc. 2002, 124, 6552-6554;
11. b) A. Endo, T. Kann, T. Fukuyama, Synlett 1999, 1103-1105.
12. J. Chen, X. Chen, M. Bois-Choussy, J. Zhu, J. Am. Chem. Soc. 2006, 128, 87-89.
13. a) S. Zheng, C. Chan, T. Furuuchi, B. J. D. Wright, B. Zhou, J. Guo, S. J. Danishefsky, Angew. Chem. 2006, 118, 1786-1791;
14. Angew. Chem. Int. Ed. 2006, 45, 1754-1759;
15. b) C. Chan, S. Zheng, B. Zhou, J. Guo, R. H. Heid, B. J. D. Wright, S. J. Danishefsky, Angew. Chem. 2006, 118, 1781-1786;
16. Angew. Chem. Int. Ed. 2006, 45, 1749-1754;
17. c) B. Zhou, S. Edmondson, S. J. Danishefsky, Tetrahedron Lett. 2000, 41, 2039-2042;
18. d) B. Zhou, J. Guo, S. J. Danishefsky, Tetrahedron Lett. 2000, 41, 2043-2046;
19. e) B. Zhou, J. Guo, S. J. Danishefsky, Org. Lett. 2002, 4, 43-46.
20. a) C. Cuevas, M. Pérez, M. J. Martin, J. L. Chicharro, C. Fernández-Rivas, M. Flores, A. Francesch, P. Gallego, M. Zarzuelo, F. De La Calle, J. Gracía, C. Polanco, I. Rodriguez, I. Manzanares, Org. Lett. 2000, 2, 2545-2548;
21. b) R. Menchaca, V. Martínez, A. Rodríguez, N. Rodríguez, M. Flores, P. Gallego, I. Manzanares, C. Cuevas, J. Org. Chem. 2003, 68, 8859-8866.
22. a) N. Saito, K. Tashiro, Y. Maru, K. Yamaguchi, A. Kubo, J. Chem. Soc. Perkin Trans. 1 1997, 53-69;
23. b) N. Saito, H. Kamayachi, M. Tachi, A. Kubo, Heterocycles 1999, 51, 9-12;
24. c) N. Saito, M. Tachi, R. Seki, H. Kamayachi, A. Kubo, Chem. Pharm. Bull. 2000, 48, 1549-1557.
25. a) B. Herberich, M. Kinugawa, A. Vazquez, R. M. Williams, Tetrahedron Lett. 2001, 42, 543-546;
26. b) W. Jin, R. M. Williams, Tetrahedron Lett. 2003, 44, 4635-4639;
27. c) W. Jin, S. Metobo, R. M. Williams, Org. Lett. 2003, 5, 2095-2098;
28. d) D. Fishlock, R. M. Williams, Org. Lett. 2006, 8, 3299-3301.
29. P. Magnus, K. S. Matthews, V. Lynch, Org. Lett. 2003, 5, 2181-2184.
30. Y.-F. Tang, Z.-Z. Liu, S.-Z. Chen, Tetrahedron Lett. 2003, 44, 7091-7094.
31. S. Aubry, S. Pellet-Rostaing, B. Fenet, M. Lemaire, Tetrahedron Lett. 2006, 47, 1319-1323.
32. P. A. Ceballos, M. Péres, C. Cuevas, A. Francesch, I. Manzanares, A. M. Echavarren, Eur. J. Org. Chem. 2006, 1926-1933.
33. R. G. Kerr, N. F. Miranda, J. Nat. Prod. 1995, 58, 1616-1621.
34. M. R. Winkle, R. C. Ronald, J. Org. Chem. 1982, 47, 2101-2108.
35. S. Hanessian, D. Delorme, Y. Dufresne, Tetrahedron Lett. 1984, 25, 2515-2518.
36. M. De Paolis, X. Chen, J. Zhu, Synlett 2004, 729-731.
37. X. Xiao, D. Bai, Synlett 2001, 535-537.
38. A. J. Mancuso, D. S. Brownfain, D. Swern, J. Org. Chem. 1979, 44, 4148-4150.
39. G. Casiraghi, M. Cornia, G. Rassu, J. Org. Chem. 1988, 53, 4919-4922.
40. a) M. De Paolis, A. Chiaroni, J. Zhu, Chem. Commun. 2003, 2896-2897;
41. b) X. Chen, J. Chen, M. De Paolis, J. Zhu, J. Org. Chem. 2005, 70, 4397-4408.
42. For a recent review, see: S. Rendler, M. Oestreich, Synthesis 2005, 1727-1747.
43. a) M. Sakaitani, Y. Ohfune, J. Org. Chem. 1990, 55, 870-876;
44. b) A. J. Zhang, D. H. Russel, J. Zhu, K. Burgess, Tetrahedron Lett. 1998, 39, 7439-7442.
45. E. D. Cox, J. M. Cook, Chem. Rev. 1995, 95, 1797-1842.
46. 2, 80%. Compound 16 has a high tendency to undergo trimerization and should be used immediately after preparation.
47. For a 1,3-cis-selective Pictet-Spengler reaction, see: a) G. Massiot, T. Mulamba, J. Chem. Soc. Chem. Commun. 1983, 1147-1149;
48. b) P. D. Bailey, S. P. Hollinshead, N. R. McLay, K. Morgan, S. J. Palmer, S. N. Prince, C. D. Reynolds, S. D. Wood, J. Chem. Soc. Perkin Trans. 1 1993, 431-439;
49. c) A. G. Myers, D. W. Kung, B. Zhong, M. Movassaghi, S. Kwon, J. Am. Chem. Soc. 1999, 121, 8401-8402;
50. d) A. G. Myers, D.W. Kung, J. Am. Chem. Soc. 1999, 121, 10828-10829.
51. One of the referees proposed that we isolate the orthoquinone methide intermediate by using N-protected starting materials to probe the reaction sequence. We are investigating in detail the mechanism of this reaction.
52. V. T. Ravikumar, A. H. Krotz, D. L. Cole, Tetrahedron Lett. 1995, 36, 6587-6590.
53. M. De Paolis, J. Blankenstein, M. Bois-Choussy, J. Zhu, Org. Lett. 2002, 4, 1235-1238.
54. For a recent comprehensive review, see: R. W. Van De Water, T. R. R. Pettus, Tetrahedron 2002, 58, 5367-5405.
55. a) F. Guibé, Y. Saint M'Leux, Tetrahedron Lett. 1981, 22, 3591-3594;
56. b) P. Four, F. Guibé, Tetrahedron Lett. 1982, 23, 1825-1828;
57. c) for a review, see: F. Guibé, Tetrahedron 1998, 54, 2967-3042.
58. Owing to the restricted availability of this family of natural products, there are very few reports in the literature that deal with SARs of these compounds, despite their medical importance; see: E. J. Martinez, T. Owa, S. L. Schreiber, E. J. Corey, Proc. Natl. Acad. Sci. USA 1999, 96, 3496-3501.