Approach towards the total synthesis of cyclopeptide alkaloids

Tetrahedron Letters

Volumn 39, Issue 3-4, 1998, Pages 283-286

  Laïb, Taoues ^a   Zhu, Jieping ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CYCLOPEPTIDE;

ARTICLE; CHIRALITY; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; REACTION TIME;

EID: 0032518633     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10513-5     Document Type: Article

References (35)

1. 1 For reviews, see: a) Schmidt, U.; Lieberknecht, A.; Haslinger, E. in the "The Alkaloids", vol 26 (Ed. Brossi, A.), Academic Press, New York, 1985, pp 299-326;
2. b) Joullié, M. M.; Nutt, R. F. in the "Alkaloids: Chemical and Biological Perspectives", vol 3 (Ed. Pelletier, S. W.), Wiley, New York, 1985, pp 113-168;
3. c) Gournelis, D. C.; Laskaris, G. G.; Verpoorte, R. Natural Product Reports 1997, 75-82.
4. 2 Païs, M.; Jarreau, F. -X.; Lusinchi, X.; Goutarel, R. Ann. Chim. (Paris) 1966, 83-105.
5. 3 (a) Schmidt, U.; Lieberknecht, A.; Bökens, H. Griesser, H. Angew. Chem. Int. Ed. Engl. 1981, 20, 1026-1027;
6. b) Schmidt, U.; Zäh, M.; Lieberknecht, A. J. Chem. Soc., Chem. Commun. 1991, 1002-1004;
7. c) Heffner, R. J.; Jiang, J.; Joullié, M. M. J. Am. Chem. Soc. 1992, 114, 10181-10189;
8. d) Han, B. H.; Kim, Y. C.; Park, M. K.; Park, J. H.; Go, H. J.; Yang, H. O.; Suh, D. Y.; Kang, Y. H. Heterocycles 1995, 41, 1909-1914.
9. 4 Lagarias, J. C.; Houghten, R. A.; Rapoport, H. J. Am. Chem. Soc. 1978, 100, 8202-8209;
10. 5 a) Schmidt, U.; Lieberknecht, A.; Griesser, H., Häusler, J. Angew. Chem. Int. Ed. Engl. 1981, 20, 281-282;
11. b) Schmidt, U.; Lieberknecht, A.; Griesser, H.; Talbiersky, J. J. Org. Chem. 1982, 47, 3261-3264.
12. 6 Heffner, R. J.; Joullié, M. M. Tetrahedron Lett. 1989, 30, 7021-7024;
13. 7 For discussion, see review cited in ref 1b.
14. 8 Lipshutz, B. H.; Huff, B. E.; McCarthy, K. E.; Miller, T. A.; Mukarram, S. M. J.; Siahaan, T. J.; Vaccaro, W. D.; Webb, H.; Falick, A. M. J. Am. Chem. Soc. 1990, 112, 7032-7041.
15. 9 For a short account, see: Zhu, J. Synlett 1997, 133-144;
16. 10 For a highlight, see: Burgess, K.; Lim, D.; Martinez, C. I. Angew. Chem. Int. Ed. Engl. 1996, 35, 1077-1078.
17. 11 Zhu, J.; Laïb, T.; Chastanet, J.; Beugelmans, R. Angew. Chem. Int. Ed. Engl. 1996, 35, 2517-2519.
18. 12 North, M. Synlett 1993, 807-820.
19. 13 Effenberger, F. Angew. Chem. Int. Ed. Engl. 1994, 33, 1555-1564.
20. 14 a) Matthews, B. R.; Jackson, W. R.; Jayatilake, G. S.; Wilshire, C.; Jacobs, H. A. Aust. J. Chem. 1988, 41, 1697-1709;
21. b) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc. Perkin Trans 1 1997, 1293-1295.
22. 15 Vergne, C.; Bois-Choussy, M.; Ouazzani, J.; Beugelmans, R.; Zhu, J. Tetrahedron Asymmetry 1997, 8, 391-398.
23. 16 Evans, D. A.; Carroll, G. L.; Truesdale, L. K. J. Org. Chem. 1974, 39, 914-917.
24. 17 a) Francalanci, F.; Cesti, P.; Cabri, W.; Bianchi, D.; Martinengo, T.; Foa, M. J. Org. Chem. 1987, 52, 5079-5082;
25. b) Gotor, V.; Brieva, R.; Rebolledo, F. J. Chem. Soc. Chem. Commu. 1988, 957-958;
26. c) Nieduzak, T. R.; Carr, A. A.; Tetrahedron: Asymmetry 1990, 1, 535-536;
27. d) Bevinakatti, H. S.; Newadkar, R. V. Tetrahedron: Asymmetry 1990, 1, 583-586.
28. 18 Takayama, S.; Moree, W. J.; Wong, C. H. Tetrahedron Lett. 1996, 37, 6287-6290.
29. 19 For recent application of Mosher's method, see: Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096. Details of our enzymatic work will be published elsewhere.
30. 20 For discussion, see: Zhu, J. Angew. Chem. Int. Ed. Engl. 1997, 36, 1074-1075.
31. 21 This is an extrapolation of the term originally proposed by Reetz, see: Reetz, M. T. Angew. Chem. Int. Ed. Engl. 1991, 30, 1531-1546.
32. 22 Laib, T. unpublished results. Details of the preparation and the cyclization of 19 will be reported in a full account,
33. 23 Lalancette, J. M.; Frêche, A.; Brindle, J. R.; Laliberté, M. Synthesis 1972, 526-532.
34. 24 Doyle, M. P.; Bryker, W. J. J. Org. Chem. 1979, 44, 1572-1574.
35. 25 Wassmundt, F. W.; Kiesman, W. F. J. Org. Chem. 1995, 60, 1713-1719.