Synthesis and biological evaluation of (-)-laulimalide analogues

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 3, 2004, Pages 575-579

  Gallagher Jr , Brian M ^a   Fang, Francis G ^a   Johannes, Charles W ^a,b   Pesant, Marc ^a   Tremblay, Martin R ^a   Zhao, Hongjuan ^a   Akasaka, Kozo ^a   Li, Xiang Yi ^a   Liu, Junke ^a   Littlefield, Bruce A ^a  

^a EISAI RESEARCH INSTITUTE   (United States)

^b Infinity Pharmaceuticals Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LAULIMALIDE; NATURAL PRODUCT;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL REACTION; DRUG ACTIVITY; DRUG SYNTHESIS; EVALUATION; RING CLOSING METATHESIS;

EID: 1642534338     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.12.001     Document Type: Article

References (40)

1. Quinoa E., Kakou Y., Crews P. J. Org. Chem. 53:1988;3642.
2. Corley D.G., Herb R., Moore R.E., Scheuer P.J., Paul V.J. J. Org. Chem. 53:1988;3644.
3. Tanaka J.-I., Higa T., Bernardinelli G., Jefford C.W. Chem. Lett. 1996;255.
4. Jefford C.W., Bernardinelli G., Tanaka J.-I., Higa T. Tetrahedron Lett. 37:1996;159.
5. Mooberry S.L., Tien G., Hernandez A.H., Plubrukarn A., Davidson B.S. Cancer Res. 59:1999;653.
6. Mooberry, S. L.; Davidson, B. S. WO 0154689, 2001.
7. Pryor D.E., O'Brate A., Bilcer G., Diaz J.F., Wang Y., Wang Y., Kabaki M., Jung M.K., Andreu J.M., Ghosh A.K., Giannakakou P., Hamel E. Biochemistry. 41:2002;9109.
8. Ghosh A.K., Wang Y. J. Am. Chem. Soc. 122:2000;11027.
9. Ghosh A.K., Wang Y. Tetrahedron Lett. 42:2001;3399.
10. Ghosh A.K., Wang Y., Kim J.T. J. Org. Chem. 66:2001;8973.
11. Paterson I., De Savi C., Tudge M. Org. Lett. 3:2001;3149.
12. Mulzer J., Ohler E. Angew. Chem., Int. Ed. 40:2001;3842.
13. Enev V.E., Kahlig H., Mulzer J. J. Am. Chem. Soc. 123:2001;10764.
14. Mulzer J., Hanbauer M. Tetrahedron Lett. 43:2002;3381.
15. Wender P.A., Hegde S.G., Hubbard R.D., Zhang L. J. Am. Chem. Soc. 124:2002;4956.
16. Crimmins M.T., Stanton M.G., Allwein S.P. J. Am. Chem. Soc. 124:2002;5958.
17. Williams D.R., Mi L., Mullins R.J., Stites R.E. Tetrahedron Lett. 43:2002;4841.
18. Nelson S.G., Cheung W.S., Kassick A.J., Hilfiker M.A. J. Am. Chem. Soc. 124:2002;13654.
19. See also Mulzer, J.; Enev, V. S. EP 1295886, 2003; Ashley, G.; Metcalf, B. WO 02064589, 2002; Ghosh, A. K. WO 03076445, 2003.
20. For a recent review, see: Crimmins M.T. Curr. Opin. Drug Disc. Dev. 5:2002;944.
21. Shimizu A., Nishiyama S. Tetrahedron Lett. 38:1997;6011.
22. Ghosh A.K., Mathivanan P., Cappiello J. Tetrahedron Lett. 38:1997;2427.
23. Shimizu A., Nishiyama S. Synlett. 1998;1209.
24. Mulzer J., Hanbauer M. Tetrahedron Lett. 41:2000;33.
25. Ghosh A.K., Wang Y. Tetrahedron Lett. 41:2000;2319.
26. Ghosh A.K., Wang Y. Tetrahedron Lett. 41:2000;4705.
27. Dorling E.K., Ohler E., Mulzer J. Tetrahedron Lett. 41:2000;6323.
28. Paterson I., De Savi C., Tudge M. Org. Lett. 3:2001;213.
29. Nadolski G.T., Davidson B.S. Tetrahedron Lett. 42:2001;797.
30. Messenger B.T., Davidson B.S. Tetrahedron Lett. 42:2001;801.
31. Dorling E.K., Ohler E., Mantoulidis A., Mulzer J. Synlett. 2001;1105.
32. Ahmed A., Ohler E., Mulzer J. Synthesis. 2001;2007.
33. Lee H.W., Jeong C.-S., Yoon S.H., Lee I.C. Bull. Korean Chem. Soc. 22:2001;791.
34. Lee H.W., Yoon S.H., Lee I.C., Chung B.Y. Bull. Korean Chem. Soc. 22:2001;1179.
35. Sivaramakrishnan A., Nadolski G.T., McAlexander I.A., Davidson B.S. Tetrahedron Lett. 43:2002;213.
36. Ahmed A., Hoegenauer E.K., Enev V.S., Hanbauer M., Kaehlig H., Ohler E., Mulzer J. J. Org. Chem. 68:2003;3026.
37. Wender P.A., Hegde S.G., Hubbard R.D., Zhang L., Mooberry S.L. Org. Lett. 5:2003;3507.
38. All yields are averages from multiple preparative-scale experiments.
39. Motoyoshi H., Ishigami K., Kitahara T. Tetrahedron. 57:2001;3899.
40. Towle M.J., Salvato K.A., Budrow J., Wels B.F., Kuznetsov G., Aalfs K.K., Welsh S., Zheng W., Seletsky B.M., Palme M.H., Habgood G.J., Singer L.A., DiPietro L.V., Wang Y., Chen J.J., Quincy D.A., Davis A., Yoshimatsu K., Kishi Y., Yu M.J., Littlefield B.A. Cancer Res. 61:2001;1013.