Synthetic studies on a phenyl-laulimalide analogue

Tetrahedron Letters

Volumn 47, Issue 47, 2006, Pages 8305-8308

  Faveau, Christelle ^a   Mondon, Martine ^a   Gesson, Jean Pierre ^a   Mahnke, Tobias ^b   Gebhardt, Sandra ^b   Koert, Ulrich ^b  

^a UNIVERSITÉ DE POITIERS   (France)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Allylboration; Laulimalide; Natural product analogues; Stereoselective synthesis; Synthesis

Indexed keywords

LAULIMALIDE DERIVATIVE; PACLITAXEL DERIVATIVE; PHENYL GROUP; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR OVERHAUSER EFFECT; RING CLOSING METATHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 33750022869     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.09.104     Document Type: Article

References (47)

1. Quinoa E., Kakou Y., and Crews P. J. Org. Chem. 53 (1988) 3642-3644
2. Corley D.G., Herb R., Moore R.E., Scheuer P.J., and Paul V.J. J. Org. Chem. 53 (1988) 3644-3646
3. Jefford C.W., Bernardinelli G., Tanaka J., and Higa T. Tetrahedron Lett. 37 (1996) 159-162
4. Tanaka J., Higa T., Bernardinelli G., and Jefford C.W. Chem. Lett. (1996) 255-256
5. Mooberry S.L., Tien G., Hernandez A.H., Plubrukarn A., and Davidson B.S. Cancer Res. 59 (1999) 653-660
6. 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., Giannakakou P., and Hamel E. Biochemistry 41 (2002) 9109-9115
7. For reviews see:. Crimmins M.T. Curr. Opin. Drug Discovery Dev. 5 (2002) 944-959
8. Mulzer J., and Öhler E. Chem. Rev. 103 (2003) 3753-3786
9. Total syntheses:. Ghosh A.K., and Wang Y. J. Am. Chem. Soc. 122 (2000) 11027-11028
10. Ghosh A.K., Wang Y., and Kim J.T. J. Org. Chem. 66 (2001) 8973-8982
11. Paterson I., De Savi C., and Tudge M. Org. Lett. 3 (2001) 213-216
12. Paterson I., De Savi C., and Tudge M. Org. Lett. 3 (2001) 3149-3152
13. Mulzer J., and Öhler E. Angew. Chem., Int. Ed. 40 (2001) 3842-3846
14. Enev V.S., Kaehlig H., and Mulzer J. J. Am. Chem. Soc. 123 (2001) 10764-10765
15. Mulzer J., and Hanbauer M. Tetrahedron Lett. 43 (2002) 3381-3383
16. Williams D.R., Mi L., Mullins R.J., and Stites R.E. Tetrahedron Lett. 43 (2002) 4841-4844
17. Crimmins M.T., Stanton M.G., and Allwein S.P. J. Am. Chem. Soc. 124 (2002) 5958-5959
18. Wender P.A., Hegde S.G., Hubbard R.D., and Zhang L. J. Am. Chem. Soc. 124 (2002) 4956-4957
19. Nelson S.G., Cheung W.S., Kassick A.J., and Hilfiker M.A. J. Am. Chem. Soc. 124 (2002) 13654-13655
20. Uenishi J., and Ohmi M. Angew. Chem., Int. Ed. 44 (2005) 2756
21. Ahmed A., Hoegenauer K., Enev V.S., Hanbauer M., Kaehlig H., Öhler E., and Mulzer J. J. Org. Chem. 68 (2003) 3026-3042
22. Wender P.A., Hegde S.G., Hubbard R.D., Zhang L., and Mooberry S.L. Org. Lett. 5 (2003) 3507-3509
23. Gallagher Jr. B.M., Fang F.G., Johannes C.W., Pesant M., Tremblay M.R., Zhao H., Akasaka K., Li X., Liu J., and Littlefield B.A. Bioorg. Med. Chem. Lett. 14 (2004) 575-579
24. Paterson I., Bergmann H., Menche D., and Berkessel A. Org. Lett. 6 (2004) 1293-1295
25. Mooberry S.L., Randall-Hlubek D.A., Leal R.M., Hegde S.G., Hubbard R.D., Zhang L., and Wender P.A. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 8803-8808
26. Gallagher Jr. B.M., Zhao H., Pesant M., and Fang F.G. Tetrahedron Lett. 46 (2005) 923-926
27. Wender P.A., Hilinski M.K., Solderman N., and Mooberry S.L. Org. Lett. 8 (2006) 1507-1510
28. Paterson I., Menche D., Hakansson A.E., Longstaff A., Wong D., Barasoain I., Bury R.M., and Diaz J.F. Bioorg. Med. Chem. Lett. 15 (2005) 2243-2247
29. Paterson I., Menche D., Britton R., Hakansson A.E., and Silva-Martinez M.A. Tetrahedron Lett. 46 (2005) 3677-3682
30. Kolb H.C., Van Nieuwenhze M.S., and Sharpless K.B. Chem. Rev. 94 (1994) 2483-2547
31. Kolb H.C., Van Nieuwenhze M.S., and Sharpless K.B. Chem. Rev. 94 (1994) 2483-2547
32. Sharpless K.B., Amberg W., Bennani Y.L., Crispino G.A., Hartung J., Jeong K.-S., Kwong H.-L., Morikawa K., Wang Z.-M., Xu D., and Zhang X.-L. J. Org. Chem. 57 (1992) 2768-2771
33. Yadav J.S., Sarkar S., and Chandrasekhar S. Tetrahedron 55 (1999) 5449-5456
34. Yamaguchi M., and Hirao I. Tetrahedron Lett. 24 (1983) 391-394
35. Chini M., Crotti P., Favero L., and Macchia F. Tetrahedron Lett. 32 (1991) 6617-6620
36. Crousse B., Alami M., and Linstrumelle G. Synlett (1997) 992-994
37. +: 537.2437, found: 537.2426.
38. Wu M.-J., Wu C.-C., and Lee P.-C. Tetrahedron Lett. 33 (1992) 2547-2548
39. Li L.-H., and Wang D. Tetrahedron Lett. 32 (1991) 2879-2882
40. Gage J.R., and Evans D.A. Org. Synth. 68 (1990) 83
41. Braun M., and Devant R. Tetrahedron Lett. 25 (1984) 5031-5034
42. Ali H.A., Goldberg I., and Srebnik M. Eur. J. Inorg. Chem. (2002) 73-78
43. Ishiyama T., Ahiko T., and Miyaura N. Tetrahedron Lett. 37 (1996) 6889-6892
44. +: 555.3258, found: 555.3263.
45. Lachance H., Lu X., Gravel M., and Hall D.G. J. Am. Chem. Soc. 125 (2003) 10160-10161
46. Inanaga J., Hirata K., Saeki H., Katsuki T., and Yamaguchi M. Bull. Chem. Soc. Jpn. 52 (1979) 1989-1993
47. +: 501.2611, found: 501.2616.