Synthesis of 8-(S)-methoxy-11-desmethyl laulimalide: A novel laulimalide analogue

Tetrahedron Letters

Volumn 46, Issue 6, 2005, Pages 923-926

  Gallagher Jr , Brian M ^a   Zhao, Hongjuan ^a   Pesant, Marc ^a   Fang, Francis G ^a  

^a NONE

Author keywords

Analogue; Laulimalide

Indexed keywords

8 METHOXY 11 NORLAULIMALIDE; LAULIMALIDE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR MODEL; STEREOCHEMISTRY;

EID: 12344321302     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.056     Document Type: Article

References (46)

1. E. Quinoa, Y. Kakou, and P. Crews J. Org. Chem. 53 1988 3642 3644
2. D.G. Corley, R. Herb, R.E. Moore, P.J. Scheuer, and V.J. Paul J. Org. Chem. 53 1988 3644
3. J.-I. Tanaka, T. Higa, G. Bernardinelli, and C.W. Jefford Chem. Lett. 1996 255 256
4. C.W. Jefford, G. Bernardinelli, J.-I. Tanaka, and T. Higa Tetrahedron Lett. 37 1996 159 162
5. S.L. Mooberry, G. Tien, A.H. Hernandez, A. Plubrukarn, and B.S. Davidson Cancer Res. 59 1999 653 660
6. Mooberry, S. L.; Davidson, B. S. WO 0154689, 2001
7. D.E. Pryor, A. O'Brate, G. Bilcer, J.F. Diaz, Y. Wang, Y. Wang, M. Kabaki, M.K. Jung, J.M. Andreu, A.K. Ghosh, P. Giannakakou, and E. Hamel Biochemistry 41 2002 9109 9115
8. E.J. Gapud, R. Bai, A.K. Ghosh, and E. Hamel Mol. Pharmacol. 66 2004 113 121
9. For related references, see: T.N. Gaitanos, R.M. Buey, J.F. Diaz, P.T. Northcote, P. Teesdale-Spittle, J.M. Andreu, and J.H. Miller Cancer Res. 64 2004 5063 5067 and
10. O. Pineda, J. Farras, L. Maccari, F. Manetti, M. Botta, and J. Vilarrasa Biorg. Med. Chem. Lett. 14 2004 4825 4829
11. A.K. Ghosh, and Y. Wang J. Am. Chem. Soc. 122 2000 11027 11028
12. A.K. Ghosh, and Y. Wang Tetrahedron Lett. 42 2001 3399 3401
13. A.K. Ghosh, Y. Wang, and J.T. Kim J. Org. Chem. 66 2001 8973 8982
14. I. Paterson, C. De Savi, and M. Tudge Org. Lett. 3 2001 3149 3152
15. J. Mulzer, and E. Ohler Angew. Chem., Int. Ed. 40 2001 3842 3846
16. V.E. Enev, H. Kahlig, and J. Mulzer J. Am. Chem. Soc. 123 2001 10764 10765
17. J. Mulzer, and M. Hanbauer Tetrahedron Lett. 43 2002 3381 3383
18. P.A. Wender, S.G. Hegde, R.D. Hubbard, and L. Zhang J. Am. Chem. Soc. 124 2002 4956 4957
19. M.T. Crimmins, M.G. Stanton, and S.P. Allwein J. Am. Chem. Soc. 124 2002 5958 5959
20. D.R. Williams, L. Mi, R.J. Mullins, and R.E. Stites Tetrahedron Lett. 43 2002 4841 4844
21. S.G. Nelson, W.S. Cheung, A.J. Kassick, and M.A. Hilfiker J. Am. Chem. Soc. 124 2002 13654 13655
22. See also: Mulzer, J.; Enev, V. S. EP 1295886, 2003
23. Ashley, G.; Metcalf, B. WO 02064589, 2002
24. Ghosh, A. K. WO 03076445, 2003
25. Ref. 6b. For recent reviews, see: M.T. Crimmins Curr. Opin. Drug Disc. Dev. 5 2002 944 959 and
26. J. Mulzer, and E. Ohler Chem. Rev. 103 2003 3753 3786
27. B.M. Gallagher Jr., F.G. Fang, C.W. Johannes, M. Pesant, M.R. Tremblay, H. Zhao, K. Akasaka, X. Li, J. Liu, and B.A. Littlefield Biorg. Med. Chem. Lett. 14 2004 575 579
28. P.A. Wender, S.G. Hegde, R.D. Hubbard, L. Zhang, and S.L. Mooberry Org. Lett. 5 2003 3507 3509
29. A. Ahmed, E.K. Hoegenauer, V.S. Enev, M. Hanbauer, H. Kaehlig, E. Ohler, and J. Mulzer J. Org. Chem. 68 2003 3026 3042
30. I. Paterson, H. Bergmann, D. Menche, and A. Berkessel Org. Lett. 6 2004 1293 1295
31. S.L. Mooberry, D.A. Randall-Hlubek, R.M. Leal, S.G. Hegde, R.D. Hubbard, L. Zhang, and P.A. Wender Proc. Natl. Acad. Sci. U.S.A. 101 2004 8803 8808
32. S. Danishefsky, and J.F. Kerwin Jr. J. Org. Chem. 47 1982 3803 3805
33. C.R. Schmid, J.D. Bryant, M. Dowlatzedah, J.L. Phillips, D.E. Prather, R.D. Schantz, N.L. Sear, and C.S. Vianco J. Org. Chem. 56 1991 4056 4058
34. 3), albeit as a ∼2:1 mixture favoring the desired isomer.
35. Q. Shen, D.G. Sloss, and D.B. Berkowitz Synth. Commun. 24 1994 1519 1530
36. W.-B. Choi, L.J. Wilson, S. Yeola, D.C. Liotta, and R.F. Schinazi J. Am. Chem. Soc. 113 1991 9377 9379
37. To the best of our knowledge, a double Stryker-type reduction of an ynone to the saturated ketone appears to be unprecedented
38. H. Motoyoshi, K. Ishigami, and T. Kitahara Tetrahedron 57 2001 3899 3908
39. 3CN at 60°C provided the shortest reaction times
40. B.T. Messenger, and B.S. Davidson Tetrahedron Lett. 42 2001 401 403
41. ref. k
42. A. Shimizu, and S. Nishiyama Synlett 1998 1209 1210
43. The stereochemistry of the newly formed center was confirmed by analysis of the R- and S-Mosher's esters. See: J.A. Dale, and H.S. Mosher J. Am. Chem. Soc. 95 1973 512 519
44. I. Ohtani, T. Kusumi, Y. Kashman, and H. Kakisawa J. Am. Chem. Soc. 113 1991 4092 4096
45. Preliminary biological evaluation of this analogue indicates it retains sub-micromolar growth inhibition potency in the MDA-MB-435 human breast cancer cell line. For assay conditions, see Ref. 5. Investigations of this analogue for activity against multidrug resistant cell lines will be reported in due course
46. A gem di-methyl strategy was undertaken in the cryptophycins to stabilize the macrolactone and faciliate process scale-up by eliminiating a sterocenter, but was also found to increase potency. See: M. Eggen, and G.I. Georg Med. Res. Rev. 22 2002 85 101