Synthetic strategy toward the C44-C65 fragment of mirabalin

Organic Letters

Volumn 16, Issue 9, 2014, Pages 2390-2393

  Echeverria, Pierre Georges ^a   Prévost, Sébastien ^a   Cornil, Johan ^b   Férard, Charlène ^a   Reymond, Sébastien ^b   Guérinot, Amandine ^b   Cossy, Janine ^b   Ratovelomanana Vidal, Virginie ^a   Phansavath, Phannarath ^a  

^a PSL RESEARCH UNIVERSITY   (France)

^b ESPCI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ANTINEOPLASTIC AGENT; MACROLIDE; MIRABALIN; RUTHENIUM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; STEREOISOMERISM; SYNTHESIS;

AMIDES; ANTINEOPLASTIC AGENTS; HYDROGENATION; MACROLIDES; MOLECULAR STRUCTURE; RUTHENIUM; STEREOISOMERISM;

EID: 84899823576     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol500720j     Document Type: Article

References (74)

1. Plaza, A.; Baker, H. L.; Bewley, C. A. J. Nat. Prod. 2008, 71, 473
2. Correction: Plaza, A.; Baker, H. L.; Bewley, C. A. J. Nat. Prod. 2009, 72, 324
3. Nishi, T.; Forgac, M. Nat. Rev. Mol. Cell. Biol. 2002, 3, 94
4. Bowman, E. J.; Gustafson, K. R.; Bowman, B. J.; Boyd, M. R. J. Biol. Chem. 2003, 278, 44147
5. Cantrell, C. L.; Gustafson, K. R.; Cecere, M. R.; Pannell, L. K.; Boyd, M. R. J. Am. Chem. Soc. 2000, 122, 8825
6. Rashid, M. A.; Cantrell, C. L.; Gustafson, K. R.; Boyd, M. R. J. Nat. Prod. 2001, 64, 1341
7. Rashid, M. A.; Gustafson, K. R.; Boyd, M. R. Tetrahedron Lett. 2001, 42, 1623
8. Chevallier, C.; Laprévote, O.; Bignon, J.; Debitus, C.; Guénard, D.; Sévenet, T. Nat. Prod. Res. 2004, 18, 479
9. Rashid, M. A.; Gustafson, K. R.; Crouch, R. C.; Groweiss, A.; Pannell, L. K.; Van, Q. N.; Boyd, M. R. Org. Lett. 2002, 4, 3293
10. Takada, K.; Choi, B. W.; Rashid, M. A.; Gamble, W. R.; Cardellina, J. H.; Van, Q. N.; Lloyd, J. R.; McMahon, J. B.; Gustafson, K. R. J. Nat. Prod. 2007, 70, 428
11. Pérez-Sayáns, M.; Somoza-Martin, J. M.; Barros-Angueira, F.; Rey, J. M.; García-García, A. Cancer Treat. Rev. 2009, 35, 707
12. Parks, S. K.; Chiche, J.; Pouysségur, J. Nature Rev. Cancer 2013, 13, 611
13. Prévost, S.; Ayad, T.; Phansavath, P.; Ratovelomanana-Vidal, V. Adv. Synth. Catal. 2011, 353, 3213
14. Prévost, S.; Phansavath, P.; Haddad, M. Tetrahedron: Asymmetry 2010, 21, 16
15. Tone, H.; Buchotte, M.; Mordant, C.; Guittet, E.; Ayad, T.; Ratovelomanana-Vidal, V. Org. Lett. 2009, 11, 1995
16. Roche, C.; Le Roux, R.; Haddad, M.; Phansavath, P.; Genêt, J.-P. Synlett 2009, 573
17. Roche, C.; Desroy, N.; Haddad, M.; Phansavath, P.; Genêt, J.-P. Org. Lett. 2008, 10, 3911
18. Blanc, D.; Madec, J.; Popowyck, F.; Ayad, T.; Phansavath, P.; Ratovelomanana-Vidal, V.; Genêt, J.-P. Adv. Synth. Catal. 2007, 349, 1592
19. Mordant, C.; Reymond, S.; Tone, H.; Lavergne, D.; Touati, R.; Ben Hassine, B.; Ratovelomanana-Vidal, V.; Genêt, J.-P. Tetrahedron 2007, 63, 6115
20. Bensoussan, C.; Rival, N.; Hanquet, G.; Colobert, F.; Reymond, S.; Cossy, J. Tetrahedron 2013, 69, 7759
21. Gallon, J.; Esteban, J.; Bouzbouz, S.; Campbell, M.; Reymond, S.; Cossy, J. Chem.-Eur. J. 2012, 18, 11788
22. Commandeur, M.; Commandeur, C.; Cossy, J. Pure Appl. Chem. 2012, 84, 1567
23. Commandeur, M.; Commandeur, C.; Cossy, J. Org. Lett. 2011, 13, 6018
24. ElMarrouni, A.; Joolakanti, S. R.; Colon, A.; Heras, M.; Arseniyadis, S.; Cossy, J. Org. Lett. 2010, 12, 4074
25. Druais, V.; Hall, M. J.; Corsi, C.; Wendeborn, S. V.; Meyer, C.; Cossy, J. Tetrahedron 2010, 66, 6358
26. Guérinot, A.; Lepesqueux, G.; Sablé, S.; Reymond, S.; Cossy, J. J. Org. Chem. 2010, 75, 5151
27. Amans, D.; Bareille, L.; Bellosta, V.; Cossy, J. J. Org. Chem. 2009, 74, 7665
28. Mandel, A. L.; Bellosta, V.; Curran, D. P.; Cossy, J. Org. Lett. 2009, 11, 3282
29. Amans, D.; Bellosta, V.; Cossy, J. Chem.-Eur. J. 2009, 15, 3457
30. Bressy, C.; Vors, J.-P.; Hillebrand, S.; Arseniyadis, S.; Cossy, J. Angew. Chem., Int. Ed. 2008, 47, 10137
31. Reymond, S.; Cossy, J. Eur. J. Org. Chem. 2006, 4800
32. Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798
33. Keck, G. E.; Palani, A.; McHardy, S. F. J. Org. Chem. 1994, 59, 3113
34. Ohkuma, T.; Kitamura, M.; Noyori, R. Asymmetric Hydrogenation. In Catalytic Asymmetric Synthesis, 2 nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 1-110.
35. Kitamura, M.; Noyori, R. Hydrogenation and Transfer Hydrogenation. In Ruthenium in Organic Synthesis; Murahashi, S.-i., Ed.; Wiley-VCH: Weinheim, 2004; pp 3-52.
36. Duprat de Paule, S.; Champion, N.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Dellis, P. French Patent 2,830,254, 2001.
37. Duprat de Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Champion, N.; Dellis, P. Tetrahedron Lett. 2003, 44, 823
38. Duprat de Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Champion, N.; Dellis, P. Eur. J. Org. Chem. 2003, 1931
39. Duprat de Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Champion, N.; Deschaux, G.; Dellis, P. Org. Process Res. Dev. 2003, 7, 399
40. Genêt, J.-P. Acc. Chem. Res. 2003, 36, 908
41. Genêt, J.-P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Caño de Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665
42. Makino, K.; Goto, T.; Hiroki, Y.; Hamada, Y. Angew. Chem., Int. Ed. 2004, 43, 882
43. Mordant, C.; Dünkelmann, P.; Ratovelomanana-Vidal, V.; Genêt, J.-P. Chem. Commun. 2004, 1296
44. Mordant, C.; Dünkelmann, P.; Ratovelomanana-Vidal, V.; Genêt, J.-P. Eur. J. Org. Chem. 2004, 3017
45. Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36
46. Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475
47. Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447
48. Stecher, H.; Faber, K. Synthesis 1997, 1
49. El Gihani, M. T.; Williams, J. M. J. Curr. Opin. Chem. Biol. 1999, 3, 11
50. Azerad, R.; Buisson, D. Curr. Opin. Chem. Biol. 2000, 11, 565
51. Ratovelomanana-Vidal, V.; Genêt, J.-P. Can. J. Chem. 2000, 78, 846
52. Huerta, F. F.; Minidis, A. B. E.; Bäckvall, J.-E. Chem. Soc. Rev. 2001, 30, 321
53. Kim, M. J.; Ahn, Y.; Park, J. Curr. Opin. Biotechnol. 2002, 13, 578
54. Pellissier, H. Tetrahedron 2003, 59, 8291
55. Vedejs, E.; Jure, M. Angew. Chem., Int. Ed. 2005, 44, 3974
56. Fogassy, E.; Nógrádi, M.; Kozma, D.; Egri, G.; Pálovics, E.; Kiss, V. Org. Biomol. Chem. 2006, 4, 3011
57. Martín-Matute, B.; Bäckvall, J. E. Curr. Opin. Chem. Biol. 2007, 11, 226
58. Pellissier, H. Tetrahedron 2008, 64, 1563
59. Pellissier, H. Adv. Synth. Catal. 2011, 353, 659
60. Ikariya, T.; Ishii, Y.; Kawano, H.; Arai, T.; Saburi, M.; Yoshikawa, S.; Akutagawa, S. J. Chem. Soc., Chem. Commun. 1985, 922
61. Ohta, T.; Tonomura, Y.; Nozaki, K.; Takaya, H.; Mashima, K. Organometallics 1996, 15, 1521
62. Mashima, K.; Nakamura, T.; Matsuo, Y.; Tani, K. J. Organomet. Chem. 2000, 607, 51
63. Jeulin, S.; Champion, N.; Dellis, P.; Ratovelomanana-Vidal, V.; Genêt, J.-P. Synthesis 2005, 3666
64. Marshall, J. A.; Adams, N. D. J. Org. Chem. 1998, 63, 3812
65. Marshall, J. A.; Mulhearn, J. J. Org. Lett. 2005, 7, 1593
66. Marshall, J. A.; Wang, X. J. Org. Chem. 1992, 57, 1242
67. Coleman, R. S.; Lu, X.; Modolo, I. J. Am. Chem. Soc. 2007, 129, 3826
68. Fleming, I.; Newton, T. W.; Roessier, F. J. Chem. Soc., Perkin Trans. 1 1981, 2527
69. Fleming, I.; Roberts, R. S.; Smith, S. C. J. Chem. Soc., Perkin Trans. 1 1998, 1209
70. Herrmann, A. T.; Martinez, S. R.; Zakarian, A. Org. Lett. 2011, 13, 3636
71. El-Faham, A.; Albericio, F. Chem. Rev. 2011, 111, 6557
72. Ilardi, E. A.; Stivala, C. E.; Zakarian, A. Org. Lett. 2008, 10, 1727
73. Takai, K.; Tagashira, M.; Kuroda, T.; Oshima, K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 6048
74. Harnying, W.; Kaiser, A.; Klein, A.; Berkessel, A. Chem.-Eur. J. 2011, 17, 4765