Simple, efficient, and modular syntheses of polyene natural products via iterative cross-coupling

Journal of the American Chemical Society

Volumn 130, Issue 2, 2008, Pages 466-468

  Suk, Joong Lee ^a   Gray, Kaitlyn C ^a   Paek, James S ^a   Burke, Martin D ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; POLYENE; AMPHOTERICIN B; ANTIFUNGAL AGENT; BIOLOGICAL PRODUCT;

ARTICLE; CHEMICAL BINDING; CROSS COUPLING REACTION; CRYSTALLIZATION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; CHEMISTRY;

AMPHOTERICIN B; ANTIFUNGAL AGENTS; BIOLOGICAL PRODUCTS; BORONIC ACIDS; POLYENES;

EID: 40149088849     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja078129x     Document Type: Article

References (65)

1. Corey, E. J.; Czakó, B.; Kürti, L. Molecules and Medicine; Wiley: New York, 2007.
2. Thirsk, C.; Whiting, A. J. Chem. Soc., Perkin Trans. I 2002, 999-1023.
3. (a) Ermishkin, L. N.; Kasumov, K. M.; Potzeluyev, V. M. Nature 1976, 262, 698-699.
4. (b) Hansel, S. D.; Hatch, C.; Ayenew, W. J. Liposome Res. 1993, 3, 377-408.
5. Palacios, D. S.; Anderson, T. M.; Burke, M. D. J. Am. Chem. Soc. 2007, 129, 13804-13805.
6. Rohmer, M.; Bouvier, P.; Ourisson, G. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 847-851.
7. (a) Luecke, H.; Schobert, B.; Richter, H.-T.; Cartailler, J.-P.; Lanyi, J. K. Science 1999, 286, 255-260.
8. (b) Kobayashi, T.; Saito, T.; Ohtani, H. Nature 2001, 414, 531-534.
9. (c) Zhong, Q.; Ruhman, S.; Ottolenghi, M.; Sheves, M.; Friedman, N.; Atkinson, G. H.; Delaney, J. K. J. Am. Chem. Soc. 1996, 118, 12828-12829.
10. (a) Cerullo, G.; Polli, D.; Lanzani, G.; De Silvestri, S.; Hashimoto, H.; Cogdell, R. J. Science 2002, 298, 2395-2398.
11. (b) Hoffman, E.; Wrench, P. M.; Sharpies, F. P.; Hiller, R. G.; Weite, W.; Diederichs, K. Science 1996, 272, 1788-1791.
12. Vershinin, A. BioFactors 1999, 10, 99-104.
13. Sklar, L. A.; Hudson, B. S.; Simoni, R. D. Proc. Natl. Acad. Sci. U.S.A. 1975, 72, 1649-1653.
14. Burton, G. W.; Ingold, K. U. Science 1984, 224, 569-573.
15. (a) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
16. (b) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; John Wiley & Sons: New York, 2002; Vol. 1.
17. (c) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442-4489.
18. (d) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
19. (e) Fürstner, A.; Nevado, C.; Waser, M.; Tremblay, M.; Chevrier, C.; Teply, F.; Aïssa, C.; Moulin, E.; Müller, O. J. Am. Chem. Soc. 2007, 129, 9150-9161.
20. Representative examples of bismetalated reagents for polyene synthesis: (a) Corey, E. J.; Wollenberg, R. H. J. Org. Chem. 1975, 40, 3788-3789.
21. (b) Lhermitte, F.; Carboni, B. Synlett 1996, 377-379.
22. (c) Lipshutz, B. H.; Lindsley, C. J. Am. Chem. Soc. 1997, 119, 4555-4556.
23. (d) Pihko, P. M.; Koskinen, A. M. P. Synlett 1999, 12, 1966-1968.
24. (e) Babudri, F.; Farinola, G. M.; Fiandanese, V.; Mazzone, L.; Naso, F. Tetrahedron 1998, 54, 1085-1094.
25. (f) Murakami, M.; Matsuda, T.; Itami, K.; Ashida, S.; Terayama, M. Synthesis 2004, 9, 1522-1526.
26. (g) Denmark, S. E.; Tymonko, S. A. J. Am. Chem. Soc. 2005, 127, 8004-8005.
27. (h) Lipshutz, B. H.; Clososki, G. C.; Chrisman, W.; Chung, D. W.; Ball, D. B.; Howell, J. Org. Lett. 2005, 7, 4561-4564.
28. (i) Coleman, R. S.; Walczak, M. C. Org. Lett. 2005, 7, 2289-2291.
29. (j) Coleman, R. S.; Lu, X.; Modolo, I. J. Am. Chem. Soc. 2007, 129, 3826-3827.
30. (a) Roush, W. R.; Brown, B. B. J. Am. Chem. Soc. 1993, 115, 2268-2278.
31. (b) Torrado, A.; Iglesias, B.; López, S.; de Lera, A. R. Tetrahedron 1995, 51, 2435-2454.
32. (a) Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2007, 129, 6716-6717.
33. (b) An alternative system for oligoarene synthesis: Noguchi, H.; Hojo, K.; Suginome, M. J. Am. Chem. Soc. 2007, 129, 758-759.
34. Hyuga, S.; Chiba, Y.; Yamashina, N.; Hara, S.; Suzuki, A. Chem. Lett. 1987, 1757-1760.
35. See Supporting Information for synthesis and characterization.
36. Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685-4696.
37. The same yield was observed whether or not this reaction was set up using a glovebox.
38. 6.
39. (a) Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508-7510.
40. (b) Takagi, J.; Takahashi, K.; Ishiyama, T.; Miyaura, N. J. Am. Chem. Soc. 2002, 124, 8001-8006.
41. (c) Billingsley, K. L.; Barder, T. E.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 5359-5363.
42. 2-Cl bonds tend to be much stronger than their Br and I counterparts, which we expect to impact favorably on the stability of polyenylhalide building blocks. For example, the bond dissociation energies for Ph-X = 96, 81, and 65 kcal/mol for X = Cl, Br, and I, respectively: Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047-1062.
43. Negishi, E.-I.; Okukado, N.; Lovich, S. F.; Luo, F.-T. J. Org. Chem. 1984, 49, 2629-2632.
44. Steric-based selective couplings with bispinacolboronic esters are known: (a) Desurmont, G.; Klein, R.; Uhlenbrock, S.; Laloë, E.; Deloux, L.; Giolando, D. M.; Kim, Y. W.; Pereira, S.; Srebnik, M. Organornetallics 1996, 15, 3323-3328.
45. (b) Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2000, 611, 392-402.
46. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
47. SM cross-couplings between vinyl chlorides and vinylboronic acids are also extremely rare. For one example, see: Organ, M. G.; Cooper, J. T.; Rogers, L. R.; Soleymanzadeh, F.; Paul, T. J. Org. Chem. 2000, 65, 7959-7970.
48. Cross-coupling-based syntheses of retinoids: (a) Negishi, E.-I.; Owczarczyk, Z. Tetrahedron Lett. 1991, 32, 6683-6686.
49. (b) See ref 13b.
50. (c) Uenishi, J.; Kawahama, R.: Yonemitsu, O.; Wada, A.; Ito, M. Angew. Chem., Int. Ed. 1998, 37, 320-323.
51. (d) Uenishi, J.; Matsui, K.; Wada, A. Tetrahedron Lett. 2003, 44, 3093-3096.
52. Romo, D.; Rzasa, R. M.; Shea, H. A.; Park, K.; Langenhan, J. M.; Sun, L.; Akhierer, A.; Liu, J. O. J. Am. Chem. Soc. 1998, 120, 12237-12254.
53. Kuerschner, L.; Ejsing, C. S.; Ekroos, K.; Schevchenko, A.; Anderson. K. I.; Thiele, C. Nat. Methods 2005, 2, 39-45.
54. (a) Wang, Y.; Ma, J.; Cheon, H.-S.; Kishi, Y. Angew. Chem., Int. Ed. 2007, 46, 1333-1336.
55. (b) Ma, J.; Cheon, H.-S.; Kishi, Y. Org. Lett. 2007, 9, 319-322.
56. Some prior syntheses of β-parinaric acid: (a) Kuklev, D. V.; Smith, W. L. Chem. Phys. Lipids 2004, 131, 215-222.
57. (b) Goerger, M. M.; Hudson, B. S. J. Org. Chem. 1988, 53, 3148-3153.
58. (c) Hayashi, T.; Oishi, T. Chem. Lett. 1985, 413-416.
59. (a) El-Etri, M.; Cuppoletti, J. Am. J. Physiol. Lung Cell. Mol. Physiol. 1996, 270, L386-L392.
60. (b) Gao, L.; Broughman, J. R.; Iwamoto, T.; Tomich, J. M.; Vemglarik, C. J.; Forman, H. J. Am. J. Physiol. Lung Cell. Mol. Physiol. 2001, 281, L24-L30.
61. (c) Jiang, C.; Lee, E. R.; Lane, M. B.; Xiao, Y.-F.; Harris, D. J.; Cheng, S. H. Am. J. Physiol. Lung Cell. Mol. Physiol. 2001, 281, L1164-L1172.
62. (d) Sidorov, V.; Kotch, F. W.; Kuebler, J. L.; Lam, Y.-F.; Davis, J. T. J. Am. Chem. Soc. 2003, 125, 2840-2841.
63. Knapp, D. M.; Gillis, E. P.; Burke, M. D. Manuscript in preparation.
64. (a) For the first and to date only reported total synthesis of AmB, see: Nicolaou, K. C.; Daines, R. A.; Chakraborty, T. K.; Ogawa, Y. J. Am. Chem. Soc. 1987, 109, 2821-2822.
65. (b) For a comprehensive review of the extensive synthetic efforts in this direction, see: Cereghetti, D. M.; Carreira, E. M. Synthesis 2006, 6, 914-942.