Asymmetric total synthesis of (-)-quinocarcin

Journal of the American Chemical Society

Volumn 130, Issue 22, 2008, Pages 7148-7152

  Wu, Yan Chao ^a   Liron, Mélanie ^a   Zhu, Jieping ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; ENANTIOSELECTIVITY; SILVER COMPOUNDS; SYNTHESIS (CHEMICAL);

AMINO THIOETHER; TETHERED SILYL ENOL ETHER; TETRACYCLIC COMPOUND;

ORGANIC COMPOUNDS;

3 HYDROXYBENZALDEHYDE; ACETALDEHYDE; ALDEHYDE; BORIC ACID; ETHER DERIVATIVE; HAFNIUM; IMINE; OCTANE; OXAZOLIDINE DERIVATIVE; PHENYLALANINE DERIVATIVE; QUINOCARCIN; SULFIDE; TERT BUTYL 2 BROMO 5 HYDROXYPHENYLALANATE; TETRAHYDROISOQUINOLINE DERIVATIVE;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL MODIFICATION; CYCLIZATION; ENANTIOSELECTIVITY; HYDROGENOLYSIS; MANNICH REACTION; OXIDATION; PICTET SPENGLER REACTION; REACTION ANALYSIS; REDUCTION; STEREOISOMERISM;

BENZALDEHYDES; ISOQUINOLINES; PHENYLALANINE; STEREOISOMERISM;

EID: 44449121406     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja800662q     Document Type: Article

References (64)

1. For a comprehensive review of the chemistry and biology of tetrahydroisoquinoline alkaloids, see: Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669-1730.
2. (a) Takahashi, K.; Shimizu, K. J. Antibiot. 1983, 463-467.
3. (b) Takahashi, K.; Tomita, F. J. Antibiot. 1983, 468-470.
4. (c) Tomita, F.; Takahashi, K.; Tamaoki, T. J. Antibiot. 1984, 1268-1272.
5. (a) Fujimoto, K.; Oka, T.; Morimoto, M. Cancer Res. 1987, 47, 1516-1522.
6. (b) Kanamaru, R.; Konishi, Y.; Ishioka, C.; Kakuta, H.; Sato, T.; Ishikawa, A.; Asamura, M.; Wakui, A. Cancer Chemother. Pharmacol. 1988, 22, 197-200.
7. (c) Saito, H.; Hirata, T.; Kasai, M.; Fujimoto, K.; Ashizawa, T.; Morimoto, M.; Sato, A. J. Med. Chem. 1991, 34, 1959-1966.
8. (d) Kahsai, A. W.; Zhu, S. T.; Wardrop, D. J.; Lane, W. S.; Fenteany, G. Chem. Biol. 2006, 13, 973-983.
9. (a) Plowman, J.; Dykers, D. J.; Narayanan, V. L.; Abbott, B. J.; Saito, H.; Hirata, T.; Grever, M. R. Cancer Res. 1995, 55, 862-867.
10. (b) Bunnell, C. A.; Supko, J. G.; Eder, J. P.; Clark, J. W.; Lynch, T. J.; Kufe, D. W.; Shulman, L. N. Cancer Chemother. Pharmacol. 2001, 48, 347-355.
11. (a) Suzuki, K.; Sato, T.; Morioka, M.; Nagai, K.; Abe, K.; Yamaguchi, H.; Saito, T. J. Antibiot. 1991, 44, 479-485.
12. (b) Ponzo, V. L.; Kaufman, T. S. J. Chem. Soc., Perkin Trans. 1 1997, 3131-3133.
13. (c) Wipf, P.; Hopkins, C. R. J. Org. Chem. 2001, 66, 3133-3139.
14. (d) Scott, J. D.; Williams, R. M. Angew. Chem., Int. Ed. 2001, 40, 1463-1465.
15. (e) Scott, J. D.; Williams, R. M. J. Am. Chem. Soc. 2002, 124, 2951-2956.
16. (a) Williams, R. M.; Flanagan, M. E.; Tippie, T. N. Biochemistry 1994, 33, 4086-4092.
17. (b) Williams, R. M.; Glinka, T.; Flanagan, M. E.; Gallegos, R.; Coffman, H.; Pei, D. H. J. Am. Chem. Soc. 1992, 110, 733-740.
18. Fukuyama, T.; Nunes, J. J. J. Am. Chem. Soc. 1988, 110, 5196-5198.
19. (a) Garner, P.; Ho, W. B.; Shin, H. J. Am. Chem. Soc. 1992, 114, 2767-2768.
20. (b) Garner, P.; Ho, W. B.; Shin, H. J. Am. Chem. Soc. 1993, 115, 10742-10753.
21. (a) Katoh, T.; Kirihara, M.; Nagata, Y;.; Kobayashi, Y.; Arai, K.; Minami, J.; Terashima, S. Tetrahedron 1994, 50, 6239-6258.
22. (b) Katoh, T.; Terashima, S. Pure Appl. Chem. 1996, 68, 703-706.
23. Kwon, S.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 16796-16797.
24. Danishefsky, S. J.; Harrison, P. J.; Webb II, R. R.; O'Neill, B. T. J. Am. Chem. Soc. 1985, 107, 1421-1423.
25. Flanagan, M. E.; Williams, R. M. J. Org. Chem. 1995, 60, 6791-6797.
26. (a) Saito, H.; Hirata, T. Tetrahedron Lett. 1987, 28, 4065-4068.
27. (b) Lessen, T. A.; Demko, D. M.; Weinreb, S. M. Tetrahedron Lett. 1990, 31, 2105-2108.
28. (c) Allway, P. A.; Sutherland, J. K.; Joule, J. A. Tetrahedron Lett. 1990, 31, 4781-4784.
29. (d) McMills, M. C.; Wright, D. L.; Zubkowski, J. D.; Valente, E. J. Tetrahedron Lett. 1996, 37, 7205-7208.
30. (e) Wipf, P.; Hopkins, C. R. J. Org. Chem. 2001, 66, 3133-3139.
31. (f) Koepler, O.; Laschat, S.; Baro, A.; Fischer, P.; Miehlich, B.; Hotfilder, M.; le Viseur, C. Eur. J. Org. Chem. 2004, 3611-3614.
32. (g) Schneider, U.; Pannecoucke, X.; Quirion, J.-C. Synlett 2005, 1853-1856.
33. Liron, M. Ph.D. Dissertation, University of Paris XI, 2006.
34. For regioselective nuclear bromination of methoxybenzene, see: Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem. 1995, 60, 5328-5331.
35. Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415.
36. (a) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595-8598.
37. (b) Lygo, B.; Andrews, B. I. Acc. Chem. Res. 2004, 37, 518-525.
38. (a) Ott, R.; Sauber, K. Tetrahedron Lett. 1972, 3873-3878.
39. (b) Trost, B. M.; Bunt, R. C.; Pulley, S. R. J. Org. Chem. 1994, 59, 4202-4205.
40. For 1,3-cis selective Pictet-Spengler reactions, see: (a) (b) Massiot, G.; Mulamba, T. J. Chem. Soc., Chem. Commun. 1983, 1147-1149.
41. (c) Bailey, P. D.; Hollinshead, S. P.; McLay, N. R.; Morgan, K.; Palmer, S. J.; Prince, S. N.; Reynolds, C. D.; Wood, S. D. J. Chem. Soc., Perkin Trans. 1, 1993, 431-439.
42. (d) Myers, A. G.; Kung, D. W.; Zhong, B.; Movassaghi, M.; Kwon, S. J. Am. Chem. Soc. 1999, 121, 8401-8402.
43. (e) Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828-10829.
44. (f) Chen, J.; Chen, X.; Bois-Choussy, M.; Zhu, J. J. Am. Chem. Soc. 2006, 128, 87-89.
45. In the absence of a 2-bromo substituent, the Pictet-Spengler reaction afforded the wrong regioisomer as a major product, see ref 10.
46. Lane, J. W.; Chen, Y.; Williams, R. M. J. Am. Chem. Soc. 2005, 127, 12684-12690.
47. Kokotos, G.; Padron, J. M.; Martin, T.; Gibbons, W. A.; Martin, V. S. J. Org. Chem. 1998, 63, 3741-3744.
48. (a) Kobayashi, S.; Ogawa, C.; Kawamura, M.; Sugiura, M. Synlett 2001, 983-985.
49. (b) Noji, M.; Ohno, T.; Fuji, K.; Futaba, N.; Tajima, H.; Ishii, K. J. Org. Chem. 2003, 68, 9340-9347.
50. (c) Sakai, N.; Asano, J.; Shimano, Y.; Konakahara, T. Synlett 2007, 2675-2678.
51. (a) Stevens, R. V. Acc. Chem. Res. 1984, 17, 289-296.
52. (b) Husson, H.-P.; Royer, J. Chem. Soc. Rev. 1999, 28, 383-394.
53. Blankenstein, J.; Zhu, J. Eur. J. Org. Chem. 2005, 1949-1964.
54. For reviews on N-acyliminium chemistry, see: (a) Hiemstra, H.; Speckamp, W. N. Comprehensive Organic Synthesis; Trost, B., Fleming, I., Heathcock, C. H., Eds.; Pergmon: Oxford, 1991; Vol. 2, pp 1047-1082.
55. (b) Maryanoff, B. E.; Zhang, H.-C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431-1628.
56. (c) Royer, J.; Bonin, M.; Micouin, L. Chem. Rev. 2004, 104, 2311-2352.
57. (a) Hiemstra, H.; Jan Vijn, R.; Speckamp, W. N. J. Org. Chem. 1988, 53, 3884-3886.
58. (b) Magnus, P.; Matthews, K. S. J. Am. Chem. Soc. 2005, 127, 12476-12477.
59. (c) Rikimaru, K.; Mori, K.; Fukuyama, T. Chem. Commun. 2005, 394-396.
60. Hiemstra and Speckamp have reported a stereospecific 5-exo-Trig cyclization; see ref 27a. In our case, only one diasteromer 28 with an exo-oriented aldehyde substituent was isolated from the cyclization of a mixture of E/Z isomers (8/1) of enol ether 27.
61. (a) Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-736.
62. (b) Johnson, C. D. Acc. Chem. Res. 1993, 26, 476-482.
63. Jia, Y.; Zhu, J. J. Org. Chem. 2006, 71, 7826-7834.
64. Evans, D. A.; Illig, C. R.; Saddler, J. C. J. Am. Chem. Soc. 1986, 108, 2478-2479.