Total synthesis and biological evaluation of 11-desmethyllaulimalide, a highly potent simplified laulimalide analogue

Organic Letters

Volumn 8, Issue 7, 2006, Pages 1507-1510

  Wender, Paul A ^a   Hilinski, Michael K ^a   Soldermann, Nicolas ^a   Mooberry, Susan L ^b  

^a STANFORD UNIVERSITY   (United States)

^b SOUTHWEST FOUNDATION FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

11 DESMETHYLLAULIMALIDE; 11-DESMETHYLLAULIMALIDE; ANTINEOPLASTIC AGENT; LAULIMALIDE; MACROLIDE; PACLITAXEL; TAXOID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG SCREENING; ECONOMICS; HELA CELL; HUMAN; IC 50; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTINEOPLASTIC AGENTS; DRUG SCREENING ASSAYS, ANTITUMOR; HELA CELLS; HUMANS; INHIBITORY CONCENTRATION 50; MACROLIDES; MOLECULAR STRUCTURE; PACLITAXEL; STRUCTURE-ACTIVITY RELATIONSHIP; TAXOIDS;

EID: 33645949745     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060233g     Document Type: Article

References (41)

1. (a) Quinoa, E.; Kakou, Y.; Crews, P. J. Org. Chem. 1988, 53, 3642.
2. (b) Corley, D. G.; Herb, R.; Moore, R. E.; Scheuer, P. J.; Paul, V. J. J. Org. Chem. 1988, 53, 3644.
3. Mooberry, S. L.; Tien, G.; Hernandez, A. H.; Plubrukarn, A.; Davidson, B. S. Cancer Res. 1999, 59, 653.
4. Pryor, D. E.; O'Brate, A.; Bilcer, G.; Diaz, J. F.; Wang, Yu; Wang, Yo; Kabaki, M.; Jung, M. K.; Andreu, J. M.; Ghosh, A. K.; Gianna-Kakou, P.; Hamel, E. Biochemistry 2002, 41, 9109.
5. Gapud, E. J.; Bai, R.; Ghosh, A. K.; Hamel, E. Mol. Pharmacol. 2004, 66, 113.
6. (a) Ghosh, A. K.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027.
7. (b) Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973.
8. (c) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 213.
9. (d) Paterson, I.; DeSavi, C.; Tudge, M. Org. Lett. 2001, 3, 3149.
10. (e) Mulzer, J.; Öhler, E. Angew. Chem., Int. Ed. 2001, 40, 3843.
11. (f) Evev, V. S.; Kaehlig, H.; Mulzer, J. J. Am. Chem. Soc. 2001, 123, 10764.
12. (g) Crimmins, M. T.; Stanton, M. G.; Allwein, S. P. J. Am. Chem. Soc. 2002, 124, 13654.
13. (h) Williams, D. R.; Mi, L.; Mullins, R. J.; Stites, R. E. Tetrahedron Lett. 2002, 43, 4841.
14. (i) Wender, P. A.; Hegde, S. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 4956.
15. (j) Nelson, S. G.; Chueng, W. S.; Kassick, A. J.; Hilfiker, M. A. J. Am. Chem. Soc. 2002, 124, 13654.
16. (j) Uenishi, J.; Ohmi, M. Angew. Chem., Int. Ed. 2005, 44, 2756.
17. (a) Ahmed, A.; Hoegenauer, K.; Enev, V. S.; Hanbauer, M.; Kaehlig, H.; Öhler, E.; Mulzer, J. J. Org. Chem. 2003, 68, 3026.
18. (b) Wender, P. A.; Hegde, S. G.; Hubbard, R. D.; Zhang, L.; Mooberry, S. L. Org. Lett. 2003, 5, 3507.
19. (c) Gallagher, B. M., Jr.; Fang, F. G.; Johannes, C. W.; Pesant, M.; Tremblay, M. R.; Zhao, H.; Akasaka, K.; Li, X.-y.; Liu, J.; Littlefield, B. A. Bioorg. Med. Chem. Lett. 2004, 14, 575.
20. (d) Paterson, I.; Bergmann, H.; Menche, D.; Berkessel, A. Org. Lett. 2004, 2, 1293;
21. Org. Lett. 2006, 8, 1511 (erratum).
22. (e) Gallagher, B. M., Jr.; Zhao, H.; Pesant, M.; Fang, F. G. Tetrahedron Lett. 2005, 46, 923.
23. (f) Paterson, I.; Menche, D.; Håkansson, A. E.; Longstaff, A.; Wong, D.; Barasoain, I.; Bury, R. M.; Díaz, J. F. Bioorg. Med. Chem. Lett. 2005, 15, 2243.
24. Mooberry, S. L.; Randall-Hlubek, D. A.; Leal, R. M.; Hegde, S. G.; Hubbard, R. D.; Zhang, L.; Wender, P. A. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 8803.
25. As determined using the MacroModel program, MM2 force field in chloroform, 10000-step Monte Carlo search.
26. 13C NMR spectra of 2 and those appearing in the Supporting Information of the Paterson publication (ref 6d). A similar incomplete correlation was seen for the penultimate intermediate 18. The published spectra were subsequently found to be incorrectly submitted. Spectra later provided by the Paterson group (Supplementary Information) are in agreement with our own and consistent with the structure of 2.
27. Huckstep, M.; Taylor, R. J. K. Synthesis 1982, 881.
28. Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403.
29. Corey, E. J.; Rücker, C. Tetrahedron Lett. 1982, 23, 719.
30. Messenger, B. T.; Davidson, B. S. Tetrahedron Lett. 2001, 42, 801.
31. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
32. Ishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490.
33. Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1976, 16, 1295.
34. See the Supporting Information for details.
35. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
36. Inaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 53, 1989.
37. A modified version of this new strategy has also been amenable to the preparation of laulimalide itself, representing a significant improvement over our total synthesis of 1. Full details will be reported elsewhere.
38. Scudiero, D. A.; Monks, A.; Sausville, E. A. J. Natl. Cancer Inst. 1998, 90, 862.
39. 50 values represent the means of three experiments ± SD.
40. Full details will be reported elsewhere.
41. This value is from ref 2.