Highly effective synthetic methods for substituted 2-arylbenzofurans using [3,3]-sigmatropic rearrangement: Short syntheses of stemofuran A and eupomatenoid 6

Organic Letters

Volumn 6, Issue 11, 2004, Pages 1761-1763

  Miyata, Okiko ^a   Takeda, Norihiko ^a   Naito, Takeaki ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; ETHER DERIVATIVE; EUPOMATENOID 6; OXIME; PHENOL; STEMOFURAN A; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL PROCEDURES; DRUG SYNTHESIS; REACTION ANALYSIS;

ACYLATION; BENZOFURANS; CYCLIZATION; ETHER, ETHYL; MOLECULAR STRUCTURE; OXIMES; PHENOLS;

EID: 2942538871     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049564o     Document Type: Article

References (34)

1. (a) Trost, B. M.; Tang, W. Angew. Chem., Int. Ed. 2002, 41, 2795-2797.
2. (b) Hamilton, C. J.; Fairlamb, A. H.; Eggleston, I. M. J. Chem. Soc., Perkin Trans, 1 2002, 1115-1123.
3. (c) Li, J.; Jeong, S.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4765-4770.
4. (d) Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4770-4773.
5. (e) Hughes, C. C.; Trauner, D. Angew. Chem., Int. Ed. 2002, 41, 1569-1572.
6. (f) Patil, A. D.; Freyer, A. J.; Killmer, L.; Offen, P.; Carte, B.; Jurewicz, A. J.; Johnson, R. K. Tetrahedron 1997, 53, 5047-5060.
7. (g) Kurosawa, W.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2003, 125, 8112-8113.
8. (h) Tamada, M.; Endo, K.; Hikino, H.; Kabuto, C. Tetrahedron Lett. 1979, 873-876.
9. Muhammad, I.; Li, X.-C.; Jacob, M. R. Tekwani, B. L.; Dunbar, D. C.; Ferreira, D. J. Nat. Prod. 2003, 66, 804-809.
10. (j) Ward, R. S. Nat. Prod. Rep. 1993, 10, 1-28.
11. (k) Ward R. S. Nat. Prod. Rep. 1995, 12, 183-205.
12. Ward, R. S. Nat. Prod. Rep. 1997, 14, 43-74.
13. (a) Friedrichsen, W. In Comprehensive Heterocyclic Chemistry II; Bird, C. W., Katritzky, A. R., Rees, C. W, Scriven, E. F. V., Eds.; Pergamon: London, 1996; Vol. 2, Chapter 2.7, pp 368-378.
14. (b) Baker, S. R.; Cases, M.; Keenan, M.; Lewis, R. A.; Tan, P. Tetrahedron Lett. 2003, 44, 2995-2999.
15. (c) Dahlén, A.; Petersson, A.; Hilmersson, G. Org. Biomol. Chem. 2003, 1, 2423-2426.
16. (d) McKiernan, G. J.; Hartley, R. C. Org. Lett. 2003, 5, 4389-4392.
17. (e) Serra, S.; Fuganti, C. Synlett 2003, 2005-2008.
18. (a) Bates, C. G.; Saejueng, P.; Murphy, J. M.; Venkataraman, D. Org. Lett. 2002, 4, 4727-4729.
19. (b) Kraus, G. A.; Zhang, N.; Verkade, J. G.; Nagarajan, M.; Kisanga, P. B. Org. Lett. 2000, 2, 2409-2410.
20. (c) Akai, S.; Morita, N.; Iio, K.; Nakamura, Y.; Kita, Y. Org. Lett. 2000, 2, 2279-2282.
21. Miyata, O.; Takeda, N.; Morikami, Y.; Naito, T. Org. Biomol. Chem. 2003, 1, 254-256.
22. Pacher, T.; Seger, C.; Engelmeier, D.; Vajrodaya, S.; Hofer, O.; Greger, H. J. Nat. Prod. 2002, 65, 820-827.
23. (a) Bowden, B. F.; Ritchie, E.; Taylor, W. C. Aust. J. Chem. 1972, 25, 2659-2669.
24. (b) Stahl, E.; Ittel, I. Planta Med. 1981, 42, 144-154.
25. (c) Freixa, B.; Vila, R.; Ferro, E. A.; Adzet, T.; Cañigueral, S. Planta Med. 2001, 67, 873-875.
26. (d) Carini, M.; Aldini, G.; Orioli, M.; Facino, R. M. Planta Med. 2002, 68, 193-197.
27. (e) Chauret, D. C.; Bernard, C. B.; Arnason, J. T.; Durst, T. J. Nat. Prod. 1996, 59, 152-155.
28. (a) Lee, J. S.; Fuchs, P. L. Org. Lett. 2003, 5, 3619-3622. (
29. b) Forbus, T. R., Jr.; Taylor, S. L.; Martin, J. C. J. Org. Chem. 1987, 52, 4156-4159.
30. When trifluoroacetic anhydride, which is the usual trifluoroacetyl agent, was used, the oxime ether could not give 2-arylbenzofuran.
31. Pasturel, J. Y.; Solladie, G.; Maignan, J. Fr. Demande FR 2833259, 2003; Chem. Abstr. 2003, 139, 36375.
32. Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org Lett., 2001, 3, 139-142.
33. McKittrick, B. A.; Stevenson, R. J. Chem. Soc., Perkin Trans. 1 1983, 475-482.
34. Bach, T.; Bartels, M. Synthesis 2003, 925-939.