Amino acid derived enamides: Synthesis and aminopeptidase activity

Organic Letters

Volumn 9, Issue 26, 2007, Pages 5617-5620

  Cesati III, Richard R ^a   Dwyer, Greg ^a   Jones, Reinaldo C ^a   Hayes, Megan P ^a   Yalamanchili, Padmaja ^a   Casebier, David S ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINO ACID; AMINOPEPTIDASE;

ARTICLE; CHEMISTRY; METABOLISM; SYNTHESIS;

AMIDES; AMINO ACIDS; AMINOPEPTIDASES;

EID: 38349167607     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7025729     Document Type: Article

References (66)

1. For selected total syntheses of the salicylate enamide macrolides, see: (a) Furstner, A.; Dierkes, T.; Thiel, O. R.; Blanda, G. Chem. Eur. J. 2001, 7, 5286.
2. (b) Nicolaou, K. C.; Kim, D. W.; Baati, R. Angew. Chem., Int. Ed. 2002, 41, 3701.
3. (c) Wang, X.; Porco, J. A., Jr. J. Am. Chem. Soc. 2003, 125, 6040.
4. For a recent review, see: Yet, L. Chem. Rev. 2003, 103, 4283.
5. Recent examples: (a) Sun, C.; Weinreb, S. M. Synthesis 2006, 3585.
6. (b) Savarin, C. G.; Boice, G. N.; Murry, J. A.; Corley, E.; DiMichele, L.; Hughes, D. Org. Lett. 2006, 8, 3903.
7. For a recent application in the synthesis of salicylihalamide A, see: Smith, A. B., III; Zheng, J. Tetrahedron 2002, 58, 6455.
8. (a) Zeeza, C. A.; Smith, M. B. Synth. Commun. 1987, 17, 729.
9. (b) Kiefel, M. J.; Maddock, J.; Pattenden, G. Tetrahedron Lett. 1992, 33, 3227.
10. (a) Brettle, R.; Mosedale, A. J. J. Chem. Soc., Perkin. Trans. 1 1988, 2, 185.
11. (b) Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407.
12. (c) Stefanuti, I.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 3735.
13. (d) Kuramochi, K.; Watanabe, H.; Kitahara, T. Synlett 2000, 397. For a recent application in the total synthesiser salicylihalamide A,
14. see: Wu, Y.; Liao, X.; Wang, R.; Xie, X.-S.; De Brabander, J. K. J. Am. Chem. Soc. 2002, 124, 3245.
15. (a) Wang, X.; Porco, J. A., Jr. J. Org. Chem. 2001, 66, 8215.
16. (b) Bayer, A.; Maier, M. E. Tetrahedron 2004, 60, 6665.
17. (a) Peterson: (i) Hudrlick, P. F.; Hudrlick, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993.
18. (ii) Cuevas, J.-C.; Patil, P.; Snieckus, V. Tetrahedron Lett. 1989, 30, 5841.
19. (iii) Palomo, C.; Aizpurua, J. M.; Legido, M.; Picard, J. P.; Dunogues, J.; Constantieux, T. Tetrahedron Lett. 1992, 33, 3903.
20. (iv) Furstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955.
21. (b) Horner-Wittig: Couture, A.; Deniau, E.; Grandclaudon, P. Tetrahedron Lett. 1993, 34, 1479.
22. (c) Wadsworth-Emmons: (i) Paterson, I.; Cowden, C.; Watson, C. Synlett 1996, 209.
23. (ii) Villa, M. V. J.; Targett, S. M.; Barnes, J. C.; Whittingham, W. G.; Marquez, R. Org. Lett. 2007, 9, 1631.
24. For a recent review, see; Dehli, J. R.; Legros, J.: Bolm, C. Chem. Commun. (Cambridge. UK) 2005, 973.
25. Sun, J.; Kozmin, S. A. Angew. Chem., Int. Ed. 2006, 45, 4991.
26. (a) Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1995, 413.
27. (b) Goossen, L. J.; Rauhaus, J. E.; Deng. G. Angew. Chem., Int. Ed. 2005, 44, 4042.
28. (a) Hosokawa, T.; Takano, M.; Kuroki, Y.; Murahashi, S.-Y. Tetrahedron Lett. 1992, 33, 6643.
29. (b) Brice, J. L.; Meerdink, J. E.; Stahl, S. S. Org. Lett. 2004, 6, 1845.
30. (c) Hansen, A. L.; Skrydstrup, T. J. Org. Chem. 2005, 70, 5997.
31. (a) Lee, J. M.; Ahn, D.-S.; Jung, D. Y.; Lee, J.; Do, Y.; Kim, S. K.; Chang, S. J. Am. Chem. Soc. 2006, 128, 12954.
32. (a) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 111.
33. (b) Wallace, D. J.; Klauber, D. J.; Chen, C.-y.; Volante, R. P. Org. Lett. 2003, 5, 4749.
34. (c) Willis, M. C.; Brace, G. N.; Holmes, I. P. Synthesis 2005, 3229.
35. (d) Klapars, A.; Campos, K. R.; Chen, C.-y.; Volante, R. P. Org. Lett. 2005, 7, 1185.
36. (e) Barluenga, J.; Moriel, P.; Aznar, F.; Valdes, C. Org. Lett. 2007, 9, 275.
37. (a) Ogawa, T.; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443.
38. (b) Shen, R.; Porco, J. A., Jr. Org. Lett. 2000, 2, 1333.
39. (c) Jiang, L.; Job, G. E.; Klapars, A.; Buchwald, S. L. Org. Lett. 2003, 5, 3667.
40. (d) Lam, P. Y. S.; Vincent, G.; Bonne, D.; Clark, C. G. Tetrahedron Lett. 2003, 44, 4927.
41. (e) Coleman, R. S.; Liu, P.-H. Org. Lett. 2004, 6, 577.
42. (f) Han, C.; Shen, R.; Su, S.; Porco, J. A., Jr. Org. Lett. 2004, 6, 27.
43. (g) Pan, X.; Cai, Q.; Ma, D. Org. Lett. 2004, 6, 1809.
44. (h) Hu, T.; Li, C. Org. Lett. 2005, 7, 2035.
45. (i) Lu, H.; Li, C. Org. Lett. 2006, 8, 5365.
46. (j) Martin, R.; Rivero, M. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 7079.
47. (k) Yuan, X.; Xu, X.; Zhou, X.; Yuan, J.; Mai, L.; Li. Y. J. Org. Chem. 2007, 72, 1510.
48. For closely related methods which involve the preparation of ynamides and their subsequent conversion to enamides, see: (a) Witulski, B.; Buschmann, N.; Bergstrasser, U. Tetrahedron 2000, 56, 8473.
49. (b) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67.
50. (c) Dunetz, J. R.; Danheiser, R. L. Org. Lett. 2003, 5, 4011.
51. (d) Zhang, X.; Zhang, Y.; Huang, J.; Hsung, R. P.; Kurtz, K. C. M.; Oppenheimer, J.; Petersen, M. E.; Sagamanova, I. K.; Shen, L.; Tracey, M. R. J. Org. Chem. 2006, 71, 4170 and references therein. For catalytic olefin isomerization methodology, see:
52. (e) Trost, B. M.; S. J.-P. Angew. Chem., Int. Ed. 2001, 40, 1468.
53. (f) Sergeyev, S. A.; Hesse, M. Helv. Chim. Acta 2003, 86, 750. For a unique rearrangement of α-silyl amides, see:
54. (g) Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 512.
55. (h) Zhang, X.; Houck, K. N.; Lin, S.; Danishefsky, S. J. J. Am. Chem. Soc. 2003, 125, 5111.
56. Harris, T. D.; Yalamanchili, P.; Cesati, R. R., III. Compounds Containing Matrix Metalloproteinase Substrates and Methods of their use. EP1691845 Al, August 23, 2006.
57. Several papers addressing enamide formation in the context of amino amides have recently appeared: (a) Yuen, J.; Fang, Y.-Q.; Lautens, M. Org. Lett. 2006, 8, 653.
58. (b) He, G.; Wang, J.; Ma, D. Org. Lett. 2007, 9, 1367.
59. (c) Toumi, M.; Couty, F.; Evano, G. Angew. Chem., Int. Ed. 2007, 46, 572.
60. (d) Toumi, M.; Couty, F.; Evano, G. J. Org. Chem. 2007, 72, 9003.
61. Given the requirement of activating functionality in current Pd-catalyzed processes, we opted for the Cu-catalyzed amidation methods such that our drug substance would be released with minimal trace of the enamide linkage. It should be noted, however, that Willis and co-workers have recently reported the Pd-catalyzed amidation of simple cyclic pseudohalides (ref 11c); extension to acyclic substrates has yet to be reported.
62. 2 with (E)-4-iodooct-4-ene (e.g., entry 3, Table 1).
63. Control experiments indicate hydantoin formation occurs after the cross-coupling event.
64. (Z)-4-Iodooct-4-ene was prepared from 4-octyne according to a popular published method: Kamiya. N.; Chikami, Y.; Ishii, Y. Synlett 1990, 675. We noted, however, the stereochemistry of HI addition was incorrectly assigned in this report; see the Supporting Information for complete details.
65. 2 was isolated in only 54% yield using these conditions.
66. For comparison to literature values, see: Niven, G. W.; Holder, S. A.; Streman, P. Appl. Microbiol. Biotechnol. 1995, 44, 100.