Regioselective entry to bromo-γ-hydroxybutenolides: Useful building blocks for assemblying natural product-like libraries

Organic Letters

Volumn 8, Issue 21, 2006, Pages 4831-4834

  Aquino, M ^a   Bruno, I ^a   Riccio, R ^a   Gomez Paloma, L ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; BROMINATED HYDROCARBON; BUTENOLIDE; DRUG DERIVATIVE; GAMMA BUTYROLACTONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

4-BUTYROLACTONE; BIOLOGICAL PRODUCTS; COMBINATORIAL CHEMISTRY TECHNIQUES; HYDROCARBONS, BROMINATED; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33750372589     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0618611     Document Type: Article

References (31)

1. (a) Gunasekera, S. P.; McCarthy, P. J.; Kelly-Borges, M.; Lobkovsky, E.; Clardy, J. J. Am. Chem. Soc. 1996, 118, 8759.
2. (b) Takahashi, M.; Dodo, K.; Sugimoto, Y.; Aoyagi, Y.; Yamada, Y.; Hashimoto, Y.; Shirai, R. Bioorg. Med. Chem. Lett. 2000, 10, 2571.
3. (a) De Silva, E. D.; Scheuer, P. J. Tetrahedron Lett. 1980, 21, 1611.
4. (b) Potts, B. C. M.; Faulkner, D. J. J. Nat. Prod. 1992, 55, 1701 .
5. (c) Potts, B. C. M.; Faulkner, D. J.; De Carvalho, M. S.; Jacobs, R. S. J. Am. Chem. Soc. 1992, 114, 5093.
6. (a) De Rosa, S.; Crispino, A.; De Giulio, A.; Iodice, C. J. Nat. Prod. 1995, 58, 1776.
7. (b) Soriente, A.; Crispino, A.; De Rosa, M.; De Rosa, S.; Scettri, A.; Scognamiglio, G.; Villano, R.; Sodano, G. Eur. J. Org. Chem. 2000, 947.
8. (c) Garcia Pastor, P.; De Rosa, S.; De Giulio, A.; Paya', M.; Alcarza, M. J. Brit. J. Pharm. 1999, 126, 301.
9. (a) Randazzo, A.; Debitus, C.; Pastor, P. G.; Alcaraz, M. J.; Paya, M.; Gomez-Paloma, L. J. Nat. Prod. 1998, 61, 571.
10. (b) Pastor, P. G.; Randazzo, A.; Gomez-Paloma, L.; Alcaraz, M. J.; Paya, M. J. Pharmacol. Exp. Ter. 1999, 289, 166.
11. (a) Katsumura, S.; Fujiwara, S.; Isoe, S. Tetrahedron Lett. 1985, 26, 5827.
12. (b) Coombs, J.; Lattmann, E.; Hoffmann, H. M. R. Synthesis 1998, 1367.
13. (c) Soriente, A.; De Rosa, M.; Apicella, A.; Scettri, A.; Sodano, G. Tetrahedron: Asymmetry 1999, 10, 4481.
14. (d) Cheung, A. K.; Murelli, R.; Snapper, M. L. J. Org. Chem. 2004, 69, 5712.
15. (a) Brohm, D.; Philippe, N.; Metzger, S.; Bhargava, A.; Müller, O.; Lieb, F.; Waldmann, H. J. Am. Chem. Soc. 2002, 124, 13171.
16. (b) Brohm, D.; Metzger, S.; Bhargava, A.; Müller, O.; Lieb, F.; Waldmann, H. Angew. Chem. 2002, 114, 319.
17. (c) Brohm, D.; Metzger, S.; Bhargava, A.; Müller, O.; Lieb, F.; Waldmann, H. Angew. Chem., Int. Ed. 2002, 41, 307.
18. Kernan, M. R.; Faulkner, D. J. J. Org. Chem. 1988, 53, 2773.
19. (a) Sodano, G.; Payà, M. et al. J. Med. Chem. 1998, 41, 3232.
20. (b) Koch, M. A.; Wittenberg, L.-O.; Basu, S.; Jeyaraj, D. A.; Gourzoulidou, E.; Reinecke, K.; Odermatt, A.; Waldmann, H. PNAS 2004, 101, 16721.
21. (c) Cheung, A. K.; Snapper, L. M. J. Am. Chem. Soc. 2002, 124, 11584.
22. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
23. (b) Wallow, T. I.; Novak, B. M. J. Org. Chem. 1994, 59, 5034.
24. Zhang, J.; Blazecka, P. G.; Belmont, D.; Davidson, J. G. Org. Lett. 2002, 25, 4559.
25. 4, did not work well in our hands.
26. (a) Corey, E. J.; Gras, J.-L.; Ulrich, P. Tetrahedron Lett. 1976, 11, 809.
27. (b) Monti, H.; Leandri, G.; Klos-Ringuet, M.; Corriol, C. Synth. Commun. 1983, 13, 1021.
28. Grieco, P. A.; Yoshikoshi, A.; Miyashita, M. J. Org. Chem. 1977, 42, 3772, and references therein.
29. (a) Larhed, M.; Lindeberg, G.; Hallberg, A. Tetrahedron Lett. 1996, 37, 8219.
30. (b) Varma, R. S.; Namboodiri, V. V. Pure Appl. Chem. 2001, 73, 1309.
31. Nagata, T.; Nakagawa, M.; Nishida, A. J. Am. Chem. Soc. 2003, 125, 7485.