Synthesis of conagenin and α-methylserine. A review

Organic Preparations and Procedures International

Volumn 40, Issue 1, 2008, Pages 67-91

  Nakano, Keiji ^a   Kotsuki, Hiyoshizo ^a   Ichikawa, Yoshiyasu ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

Α-METHYLSERINE;

AMINO ACIDS;

EID: 41149090615     PISSN: 00304948     EISSN: 19455453     Source Type: Journal    
DOI: 10.1080/00304940809356641     Document Type: Article

References (58)

1. T. Yamashita, M. Iijima, H. Nakamura, K. Isshiki, H. Naganawa, S. Hattori, M. Hamada, M. Ishizuka, T. Takeuchi, and Y. Iitaka, J. Antibiot., 44, 557 (1991).
2. M. Ishizuka, M. Kawatsu, T. Yamashita, M. Ueno, and T. Takeuchi, Int. J. Immunopharmac., 17, 133 (1995).
3. S. Hatakeyama, H. Fukuyama, Y. Mukugi, and H. Irie, Tetrahedron Lett., 37,4047 (1996).
4. D. Enders, M. Bartsch, and J. Runsink, Synthesis, 243 (1999).
5. S. Sano, T. Miwa, K. Hayashi, K. Nozaki, Y. Okazaki, and Y. Nagao, Tetrahedron Lett., 42, 4029 (2001).
6. Y. Matsukawa, M. Isobe, H. Kotsuki, and Y. Ichikawa, J. Org. Chem., 70, 5339 (2005).
7. T. Yakura, Y. Yoshimoto, C. Ishida, and S. Mabuchi, Synlett, 930 (2006).
8. T. K. Chakraborty and G. Sudhakar Tetrahedron Lett., 47, 5847 (2006).
9. I. Paterson, J. M. Goodman, M. A. Listner, R. C. Schumann, C. K. McClure, and R. D. Norcross, Tetrahedron, 46,4663 (1990).
10. M. T. Nunez and V. S. Martin, J. Org. Chem., 55, 1928 (1990).
11. D. Enders, M. Bartsch, and J. Runsink, Angew. Chem. Int. Ed. Engl., 33, 2098 (1994);
12. D. Enders, M. Bartsch, and J. Runsink, Tetrahedron, 52, 1503 (1996).
13. J. Tsuji, I. Shimizu, and K. Yamamoto, Tetrahedron Lett., 34, 2975 (1976).
14. Y. Mori, M. Kuhara, A. Takeuchi, and M. Suzuki, Tetrahedron Lett., 29, 5419 (1988).
15. T. Iversen and D. R. Bundle, J. Chem. Soc. Chem. Commun., 1240 (1981);
16. A. B. Smith III, S. M. Condon, J. A. McCauley, J. L. Leazer, J. W. Leahy, and R. E. Maleczka, J. Am. Chem. Soc., 119, 947 (1997).
17. D. H. R. Barton, W. B. Motherwell, and A. Stange, Synthesis, 743 (1981).
18. F. Eustache, P. I. Dalko, and J. Cossy, Org. Lett., 4, 1263 (2002).
19. T. Nakata, Y. Tani, M. Hatozaki, and T. Oishi, Chem. Pharm. Bull., 32, 1411 (1984).
20. M. Nakano, W. Kikuchi, J. Matsuo, and T. Mukaiyama, Chemistry Lett., 424 (2001).
21. T. K. Chakraborty and D. Das, Tetrahedron Lett., 43,2313 (2002);
22. T. K. Chakraborty, D. Thippeswamy, V. R. Suresh, and S. Jayaprakash, Chemistry Lett., 563 (1997).
23. A. Kovdcs-Kulyassa, P. Herczegh, and F. J. Sztaricskai, Tetrahedron Lett., 37, 2499 (1996).
24. J. R. Snyder and A. S. Serianni, Carbohydr. Res., 163,169 (1987).
25. B. M. Bachmann and D. Seebach, Helv. Chim. Acta, 81, 2430 (1998).
26. J. A. R. Rodrigues, P. J. S. Moran, C. D. F. Milagre, and C. V. Ursini, Tetrahedron Lett., 45, 3579 (2004).
27. H. H. Wasserman and W.-B. Ho, J. Org. Chem., 59,4364 (1994).
28. U. Groth, Y.-C. Chiang, and U. Shollkopf, Liebigs Ann. Chem., 1756 (1982).
29. U. Shollkopf, U. Groth, C.-O. Westphalen, and C. Deng, Synthesis, 969 (1981).
30. D. Seebach and J. D. Aebi, Tetrahedron Lett., 25, 2545 (1984);
31. D. Seebach, R. Imwinkelried, and T. Weber, in; “Modem Synthetic Method” R. Scheffold Ed., Springer-Verlag, Berlin Heidelberg New York Tokyo, 1986, Vol. 4, PP. 148-191.
32. P.-J. Colson and L. S. Hegedus, J. Org. Chem., 58, 5918 (1993).
33. L. S. Hegedus, R. Imwinkelried, M. Alarid-Sargent, D. Dvorak, and Y. Satoh, J. Am. Chem. Soc., 112,1109(1990).
34. S.-H. Moon and Y. Ohfune, J. Am. Chem. Soc., 116, 7405 (1994).
35. P. Wipf, S. Venkatraman, and C. P. Miller, Tetrahedron Lett., 36, 3639 (1995).
36. W. E. McEwen, W. E. Conrad, and C. A. VanderWerf, J. Am. Chem. Soc., 74, 1168 (1952);
37. Y. Ittah, Y. Sasson, I. Shahak, S. Tsaroom, and J. Blum, J. Org. Chem. 43,4271 (1978);
38. J. Legters and L. Thijs, B. Zwanenburg, Reel. Trav. Chim. Pays-Bas, 111, 1 (1992).
39. S. Hatakeyama, H. Matsumoto, H. Fukuyama, Y. Mukugi, and H. Irie, J. Org. Chem., 62, 2275 (1997).
40. J. A. Marco, M. Carda, J. Murga, F. González, and E. Falomir, Tetrahedron Lett., 38, 1841 (1997);
41. M. Carda, J. Murga, S. Rodríguez, F. González, E. Castillo, and J. A. Marco, Tetrahedron: Asymmetry, 9, 1703 (1998);
42. Portolés, J. Murga, E. Falomir, M. Carda, S. Uriel, and J. A. Marco, Synlett, 711 (2002);
43. J. Murga, R. Portolés, E. Falomir, M. Carda, and J. A. Marco, Tetrahedron: Asymmetry, 16, 1807 (2005).
44. J. A. Marco, M. Carda, F. González, S. Rodriguez, and J. Murga, Liebigs Ann., 1801 (1996).
45. A. Avenoza, C. Cativiela, F. Corzana, J. M. Peregrina, D. Sucunza, and M. M. Zurbano, Tetrahedron: Asymmetry, 12, 949 (2001);
46. A. Avenoza, J. M. Peregrina, and E. S. Martin, Tetrahedron Lett., 44, 6413 (2003).
47. B. M. Kim and K. B. Sharpless, Tetrahedron Lett., 31, 4317 (1990);
48. B. B. Lohray, Synthesis, 1035 (1992);
49. H.-S. Byun, L. He, and R. Bittman, Tetrahedron, 56, 7051 (2000).
50. Y. Ichikawa, J. Chem. Soc. Perkin Trans. I, 2135 (1992);
51. I. A. O’Neil, in: “Comprehensive Organic Functional Group Transformations”, A. Katritzky, O. Meth-Cohn, C. W. Ress, Eds., Pergamon, Oxford, 1995, Vol. 3, P. 696.
52. C. G. Espino and J. DuBois, Angew. Chem. Int. Ed., 40, 598 (2001);
53. A. Hinman and J. DuBois, J. Am. Chem. Soc., 125,11510 (2003);
54. K. A. Parker and W. Chang, Org. Lett., 5, 3891 (2003);
55. K. A. Parker and W. Chang, Org. Lett., 7, 1785 (2005);
56. R. Nodner, B. K. Marcellino, A. Sererino, A. L. Smenton, and C. M. Rojas, J. Org. Chem., 70, 3988 (2005);
57. H. M. L. Davies and M. S. Long, Angew. Chem. Int. Ed., 44, 3518 (2005).
58. T. Ishizuka and T. Kunieda, Tetrahedron Lett., 28,4185 (1987).