A rapid access to biaryl ether containing macrocycles by pairwise use of Ugi 4CR and intramolecular SNAr-based cycloetherification

Organic Letters

Volumn 3, Issue 25, 2001, Pages 4079-4082

  Cristau, Pierre ^a   Vors, Jean Pierre ^b   Zhu, Jieping ^a  

^a CNRS   (France)

^b BAYER CROPSCIENCE AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM CHLORIDE; ETHER DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

AMMONIUM CHLORIDE; CYCLIZATION; ETHERS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SOLVENTS; SUPPORT, NON-U.S. GOV'T;

EID: 0035856895     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0168420     Document Type: Article

References (51)

1. (a) Williams, D. H.; Bardsley, B. Angew. Chem., Int. Ed. Engl. 1999, 38, 1173-1193.
2. (b) Zhu, J. Exp. Opin. Ther. Pat. 1999, 9, 1005-1019.
3. (a) Itokawa, H.; Takeya, K. Heterocycles 1993, 35, 1467-1501.
4. (b) Itokawa, H.; Takeya, K.; Hitotsuyanagi, Y.; Morita, H. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1997; Vol 49, pp 301-387.
5. (a) Kase, H.; Kaneko, M.; Yamada, K. J. Antibiot. 1987, 40, 450-454.
6. (b) Yasuzawa, T.; Shirahata, K.; Sano, H. J. Antibiot. 1987, 40, 455-458.
7. (a) Tamai, S.; Kaneda, M.; Nakamura, S. J. Antibiot. 1982, 35, 1130-1136.
8. (b) Kaneda, M.; Tamai, S.; Nakamura, S.; Hirata, T.; Kushi, Y.; Suga, T. J. Antibiot. 1982, 35, 1137-1140.
9. Seya, H.; Nozawa, K.; Nakajima, S.; Kawai, K.-I.; Udagawa, S.-I. J. Chem. Soc., Perkin Trans. 1 1986, 109-116.
10. For a review, see: Nicolaou, K. C.; Boddy, C. N. C.; Bräse, S.; Winssinger, N. Angew. Chem., Int. Ed. 1999, 38, 2096-2152.
11. (a) Rao, A. V. R.; Gurjar, M. K.; Reddy, L.; Rao, A. S. Chem. Rev. 1995, 95, 2135-2167.
12. (b) Sawyer, J. S. Tetrahedron 2000, 56, 5045-5065.
13. Recent exemples: (a) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032.
14. (b) Dinsomore, C. J.; Bogusky, M. J.; Culberson, J. C.; Bergman, J. M.; Homnick, C. F.; Zartman, C. B.; Mosser, S. D.; Schaber, M. D.; Robinson, R. G.; Koblan, K. S.; Huber, H. E.; Graham, S. L.; Hartman, G. D.; Huff, J. R.; Williams, T. M. J. Am. Chem. Soc. 2001, 123, 2107-2108.
15. Dolle, R. E. J. Comb. Chem. 2000, 2, 383-433.
16. Zhu, J. Synlett 1997, 133-144.
17. (a) Burgess, K. Lim, D.; Bois-Choussy, M.; Zhu, J. Tetrahedron Lett. 1997, 38, 3345-3348.
18. (b) Fotsch, C.; Kumaravel, G.; Sharma, S. K.; Wu, A. D.; Gounarides, J. S.; Nirmala, N. R.; Petter, R. C. Bioorg. Med. Chem. Lett. 1999, 9, 2125-2130.
19. (c) Goldberg, M.; Smith, L., II; Yamayo, N.; Kiselyov, A. S. Tetrahedron 1999, 55, 13887-13898.
20. (d) Jefferson, E. A.; Swayze, E. E. Tetrahedron Lett. 1999, 40, 7757-7760.
21. TTN-mediated cycloetherification on solid support, see: (a) Nakamura, K.; Nishiya, H.; Nishiyama, S. Tetrahedron Lett. 2001, 42, 6311-6313.
22. (b) Yamamura, S.; Nishiyama, S. J. Synth. Org. Chem. Jpn. 1997, 55, 1029-1039.
23. Zhao, G.; Sun, X.; Bienaymé, H.; Zhu. J. J. Am. Chem. Soc. 2001, 123, 6700-6701.
24. (a) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123-131.
25. (b) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
26. (c) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmidtt, P. Chem. Eur. J. 2000, 6, 3321-3329.
27. Selected examples of Ugi 4CR/post functionalization, see: (a) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574-2583.
28. (b) Hulme, C.; Peng, J.; Tang, S. Y.; Burns, C. J.; Morize, I.; Labaudiniere, R. J. Org. Chem. 1998, 63, 8021-8023.
29. (c) Fokas, D.; Ryan, W. J.; Casebier, D. S.; Coffen, D. G. Tetrahedron Lett. 1998, 39, 2235-2238.
30. (d) Hulme, C.; Cherrier, M. P. Tetrahedron Lett. 1999, 40, 5295-5299.
31. (e) Biénaymé, H.; Bouzid, K. Tetrahedron Lett. 1999, 40, 2735-2738.
32. (f) Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851-1854.
33. (g) Hulme, C.; Ma, L.; Cherrier, M.-P.; Romano, J. J.; Morton, G.; Duquenne, C.; Salvino, J.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1883-1887.
34. (h) Lee, D.; Sello, J. K.; Schreiber, S. L. Org. Lett. 2000, 2, 709-712.
35. (i) Beck, B.; Magnin-Lachaux, M.; Herdtweck, E.; Dömling, A. Org. Lett. 2001, 3, 2875-2878.
36. Tempest, P.; Ma, V., Kelly, M. G.; Jones, W.; Hulme, C. Tetrahedron Lett. 2001, 42, 4963-4968.
37. Beugelmans, R.; Singh, G. P.; Bois-Choussy, M.; Chastanet, J.; Zhu, J. J. Org. Chem. 1994, 59, 5535-5542.
38. Cooper, M. S.; Seton, A. W.; Stevens, M. F.; Westwell, A. D. Bioorg. Med. Chem. Lett. 1996, 6, 2613-1616.
39. Obrecht, R.; Herrmann, R.; Ugi, I. Synthesis 1984, 400-402.
40. Bowers, M. M.; Carroll, P.; Joullié, M. M. J. Chem. Soc., Perkin Trans. 1 1989, 857-865.
41. Beugelmans, R.; Bigot, A.; Zhu, J. Tetrahedron Lett. 1994, 35, 5649-5652.
42. The failure of the Ugi reaction in MeOH has been observed in other cases, see, for example: Neyer, G.; Achatz, J.; Danzer, B.; Ugi, I. Heterocycles 1990, 30, 863-869.
43. (a) Bienaymé, H.; Bouzid, K. Angew. Chem., Int. Ed. 1998, 37, 2234-2237.
44. (b) Park, S. J.; Keum, G.; Kang, S. B.; Koh, H. Y.; Kim, Y. Tetrahedron Lett. 1998, 39, 7109-7112.
45. Since refluxing using Dean-Stark apparatus is inconvenient from the perspective view of parallel synthesis, only toluene was investigated further.
46. Positive effect of LiBr in a three-component synthesis of tetracyclic tetrahydroisoqunoline, see: Gonzalez-Zamora, E.; Fayol, A.; Bois-Choussy, M.; Chiaroni, A.; Zhu, J. J. Chem. Soc., Chem. Commun. 2001, 1684-1685.
47. (a) Matier, W. L.; Owens, D. A.; Comer, W. T.; Deitchman, D.; Ferguson, H. C.; Seidehamel, R. J.; Young, J. R. J. Med. Chem. 1973, 16, 901-908.
48. (b) Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768-1769.
49. For an earlier study concerning the salt effect on the Ugi reaction, see: McFarland, J. M. J. Org. Chem. 1963, 28, 2179-2181.
50. 2, heptane/EtOAc = 60/40) to afford 5a (67 mg, 60%) as a mixture of two diastereoisomers (1/1 ratio).
51. For examples of atropselective cycloetherification, see ref 6 and Bois-Choussy, M.; Neuville, L.; Beugelmans, R.; Zhu, J. J. Org. Chem. 1996, 61, 9309-9322.