First asymmetric total synthesis of Us-7 and -8, novel D-seco Corynanthe-type oxindole alkaloids from uncaria attenuata: Structure revision of Us-7 and determination of absolute stereochemistry

Organic Letters

Volumn 5, Issue 16, 2003, Pages 2967-2970

  Takayama, Hiromitsu ^a   Fujiwara, Rika ^a   Kasai, Yasuko ^a   Kitajima, Mariko ^a   Aimi, Norio ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; OXINDOLE;

ABSORPTION; ARTICLE; ASSAY; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; STEREOCHEMISTRY;

EID: 0141855174     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035128a     Document Type: Article

References (45)

1. Aimi, N.; Shimizu, T.; Sada, H.; Takayama, H.; Sakai, S.; Wongseripipatana, S.; Ponglux, D. J. Chem. Soc., Perkin Trans. 1 1997, 187.
2. (a) Ponglux, D.; Supavita, T.; Verpoorte, R.; Phillipson, J. D. Phytochemistry 1980, 19, 2013.
3. (b) Ponglux, D.; Wongseripipatana, S.; Aimi, N.; Nishimura, M.: Ishikawa, M.; Sada, H.; Haginiwa, J.; Sakai, S. Chem. Pharm. Bull. 1990, 38, 573.
4. (c) Takayama, H.; Shimizu, T.; Sada, H.; Harada, Y.; Kitajima, M.; Aimi, N. Tetrahedron 1999, 55, 6841.
5. (a) Pousset, J.-L.; Poisson, J.; Shine, R. J.; Shamma, M. Bull. Soc. Chim. Fr. 1967, 2766. (b) Trager, W. F.; Lee, C. M.; Phillipson, J. D.; Haddock, R. E.; Dwumabadu, D.; Beckett, A. H. Tetrahedron 1968, 24, 523.
6. (b) Trager, W. F.; Lee, C. M.; Phillipson, J. D.; Haddock, R. E.; Dwumabadu, D.; Beckett, A. H. Tetrahedron 1968, 24, 523.
7. Laus, G.; Wurst, K. Helv. Chim. Acta 2003, 86, 181 and references therein.
8. For reviews, see: (a) Herbert, R. B. In The Monoterpenoid Indole Alkaloids; supplement to Vol. 25, Part 4 of The Chemistry of Heterocyclic Compounds; Saxton, J. E., Ed.; Wiley: Chichester, 1994; Chapter 1. (b) Kutchan, T. M. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 50, Chapter 7. (c) Takayama, H.; Sakai, S. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 50, Chapter 11.
9. For reviews, see: (a) Herbert, R. B. In The Monoterpenoid Indole Alkaloids; supplement to Vol. 25, Part 4 of The Chemistry of Heterocyclic Compounds; Saxton, J. E., Ed.; Wiley: Chichester, 1994; Chapter 1. (b) Kutchan, T. M. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 50, Chapter 7. (c) Takayama, H.; Sakai, S. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 50, Chapter 11.
10. For reviews, see: (a) Herbert, R. B. In The Monoterpenoid Indole Alkaloids; supplement to Vol. 25, Part 4 of The Chemistry of Heterocyclic Compounds; Saxton, J. E., Ed.; Wiley: Chichester, 1994; Chapter 1. (b) Kutchan, T. M. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 50, Chapter 7. (c) Takayama, H.; Sakai, S. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 50, Chapter 11.
11. (a) Vigneron, J. P.; Blanchard, J. M. Tetrahedron Lett. 1980, 21, 1739.
12. (b) Tsuboi, S.; Sakamoto, J.; Yamashita, H.; Sakai, T.; Utaka, M. J. Org. Chem. 1998, 63, 1102.
13. (c) Bertus, P.; Phansavath, P.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Touati, A. R.; Homri, T.; Ben Hassine, B. Tetrahedron: Asymmetry 1999, 10, 1369.
14. (d) Tiecco, M.; Testaferri, L.; Marini, F.; Sternativo, S.; Bagnoli, L.; Santi, C.; Temperini, A. Tetrahedron: Asymmetry 2001, 12, 1493.
15. Cywin, C. L.; Webster, F. X.; Kallmerten, J. J. Org. Chem. 1991, 56, 2953.
16. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
17. Fukuyama, T.; Lin, S.-C.; Li, L. J. Am. Chem. Soc. 1990, 112, 7050.
18. Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 4171.
19. Holton, R. A.; Zhang, Z.; Clarke, P. A.; Nadizadeh, H.; Procter, D. J. Tetrahedron Lett. 1998, 39, 2883.
20. Kisfaludy, L.; Otvos, L. Jr. Synthesis 1987, 510.
21. (a) Finch, N.; Gemenden, C. W.; Hsu, I. H.-C.; Taylor, W. I. J. Am. Chem. Soc. 1963, 85, 1520.
22. (b) Finch, N.; Gemenden, C. W.; Hsu, I. H.-C.; Kerr, A.; Sim, G. A.; Taylor, W. I. J. Am. Chem. Soc. 1965, 87, 2229.
23. (a) Finch, N.; Taylor, W. I. J. Am. Chem. Soc. 1962, 84, 3871.
24. (b) Shavel, J., Jr.; Zinnes, H. J. Am. Chem. Soc. 1962, 84, 1320.
25. (c) Hollinshead, S. P.; Grubisha, D. S.; Bennett, D. W.; Cook, J. M. Heterocycles 1989, 29, 529.
26. (d) Martin, S. F.; Mortimore, M. Tetrahedron Lett. 1990, 31, 4557.
27. (e) Stahl, R.; Borschberg, H.-J.; Acklin, P. Helv. Chim. Acta 1996, 79, 1361.
28. (f) Martin, S. F.; Clark, C. W.; Ito, M.; Mortimore, M. J. Am. Chem. Soc. 1996, 118, 9840.
29. (g) Ito, M.; Clark, C. W.; Mortimore, M.; Goh, J. B.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 8003.
30. (a) Van Tamelen, E. E.; Yardley, J. P.; Miyano, M.; Hinshaw, W. B., Jr. J. Am. Chem. Soc. 1969, 91, 7333.
31. (b) Pellegrini, C.; Strassler, C.; Weber, M.; Borschberg, H. J. Tetrahedron: Asymmetry 1994, 5, 1979.
32. (c) Edmondson, S.; Danishefsky, S. J.; Sepp-Lorenzino, L.; Rosen, N. J. Am. Chem. Soc. 1999, 121, 2147.
33. (a) Esmond, R. W.; Le Quesne, P. W. J. Am. Chem. Soc. 1980, 102, 7117.
34. (b) Takayama, H.; Masubuchi, K.; Kitajima, M.; Aimi, N.; Sakai, S. Tetrahedron 1989, 45, 1327.
35. (c) Takayama, H.; Kitajima, M.; Ogata, K.; Sakai, S. J. Org. Chem. 1992, 57, 4583.
36. (d) Peterson, A. C.; Cook, J. M. Tetrahedron Lett. 1994, 35, 2651.
37. (e) Peterson, A. C.; Cook, J. M. J. Org. Chem. 1995, 60, 120.
38. (f) Wearing, X. Z.; Cook, J. M. Org. Lett. 2002, 4, 4237 and references therein.
39. (a) Wenkert, E.; Udelhofen, J. H.; Bhattacharyya, N. K. J. Am. Chem. Soc. 1959, 81, 3763.
40. (b) Seaton, J. C.; Nair, M. D.; Edwards, O. E.; Marion, L. Can. J. Chem. 1960, 38, 1035.
41. (c) Phillipson, J. D.; Hemingway, S. R. Phytochemistry 1973, 12, 2795.
42. (d) Awang, D. V. C.; Vincent, A.; Kindack, D. Can. J. Chem. 1984, 62, 2667.
43. (e) Laus, G. J. Chem. Soc., Perkin Trans. 2 1998, 315.
44. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
45. Yamada, K.; Takeda, M.; Iwakuma, T. J. Chem. Soc., Perkin Trans. 1 1983, 265.