Divergent structural complexity from a linear reaction sequence: Synthesis of fused and spirobicyclic γ-lactams from common synthetic precursors

Journal of Combinatorial Chemistry

Volumn 8, Issue 3, 2006, Pages 293-296

  Masse, Craig E ^a,b   Ng, Pui Yee ^a   Fukase, Yoshiyuki ^a   Sánchez Roselló, María ^a   Shaw, Jared T ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; BICYCLO COMPOUND; LACTAM; SPIRO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANTI-BACTERIAL AGENTS; BICYCLO COMPOUNDS; CHEMISTRY, PHARMACEUTICAL; COMBINATORIAL CHEMISTRY TECHNIQUES; LACTAMS; MOLECULAR STRUCTURE; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 33744477937     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc050153o     Document Type: Article

References (34)

1. (a) Tan, D. S. Nat. Chem. Biol. 2005, 1, 74-84.
2. (b) Shang, S.; Tan, D. S. Curr. Opin. Chem. Biol. 2005, 9, 248-258.
3. (a) Schreiber, S. L. Nat. Chem. Biol. 2005, 1, 64-66.
4. (b) Lipinski, C. A. Drug Discovery Today: Technol. 2004, 1, 337-341.
5. (c) Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997-8.
6. (d) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
7. (e) Blackwell, H. E.; Perez, L.; Stavenger, R. A.; Tallarico, J. A.; Cope Eatough, E.; Foley, M. A.; Schreiber, S. L. Chem. Biol. 2001, 8, 1167-1182.
8. (f) Clemons, P. A.; Koehler, A. N.; Wagner, B. K.; Sprigings, T. G.; Spring, D. R.; King, R. W.; Schreiber, S. L.; Foley, M. A. Chem. Biol. 2001, 8, 1183-1195.
9. (g) Hall, D. G.; Manku, S.; Wang, F. J. Comb. Chem. 2001, 3, 125-150.
10. (h) Burdine, L.; Kodadek, T. Chem. Biol. 2004, 11, 593-597.
11. (i) Spring, D. R. Chem. Soc. Rev. 2005, 34, 472-482.
12. Nicolaou, K. C.; Snyder, S. A. Angew. Chem., Int. Ed. 2005, 44, 1012-1044.
13. Rivkin, A.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2005, 44, 2838-2850.
14. (a) Castagnoli, N., Jr.; Cushman, M. J. Org. Chem. 1971, 36, 3404-3406.
15. (b) Cushman, M.; Madaj, E. J. J. Org. Chem. 1987, 52, 907-915.
16. See, for example: (a) Cushman, M.; Abbaspour, A.; Gupta, Y. P. J. Am. Chem. Soc. 1983, 105, 2873-2879.
17. (b) Cushman, M.; Choong, T.-C.; Valko, J. T.; Koleck, M. P. J. Org. Chem. 1980, 45, 5067-5073.
18. (c) Cushman, M.; Cheng, L. J. Org. Chem. 1978, 43, 286-288.
19. For a conceptually similar reaction sequence, see: Cuny, G.; Bois-Choussy, M.; Zhu, J. J. Am. Chem. Soc. 2004, 126, 14475-14484.
20. Mitchell, J. M.; Shaw, J. T. Angew. Chem., Int. Ed. 2006, 45, 1722-1726.
21. Spiro-oxindoles 8-10: (a) Edmondson, S.; Danishefsky, S. J.; Sepp-Lorenzino, L.; Rosen, N. J. Am. Chem. Soc. 1999, 121, 2147-2155.
22. (b) Wrobel, J.; Dietrich, A.; Woolson, S. A.; Millen, J.; McCaleb, M.; Harrison, M. C.; Hohman, T. C.; Sredy, J.; Sullivan, D. J. Med. Chem. 1992, 35, 4613-4627.
23. (c) Ponglux, D.; Wongseripipatana, S.; Aimi, N.; Nishimura, M.; Ishikawa, M.; Sada, H.; Haginiwa, J.; Sakai, S. Chem. Pharm. Bull. 1990, 38, 573-575.
24. For a review of related structures, see: (d) Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209-2219.
25. Fused tricyclic compounds 11-13: (e) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129-132.
26. (f) Witherup, K. M.; Ransom, R. W.; Graham, A. C.: Bernard, A. M.; Salvatore, M. J.; Lumma, W. C.; Anderson, P. S.; Pitzenberger, S. M.; Varga, S. L. J. Am. Chem. Soc. 1995, 117, 6682-6685.
27. (g) Ife, R. J.; Brown, T. H.; Blurton, P.; Keeling, D. J.; Leach, C. A.; Meeson, M. L.; Parsons, M. E.; Theobald, C. J. J. Med. Chem. 1995, 38, 2763-2773.
28. (a) Kim, Y.-K.; Arai, M. A.; Arai, T.; Lamenzo, J. O.; Dean, E. F., III; Patterson, N.; Clemons, P. A.; Schreiber, S. L. J. Am. Chem. Soc. 2004, 126, 14740-14745.
29. (b) Sauer, W. H. B.; Schwarz, M. K. J. Chem. Inf. Comput. Sci. 2003, 43, 987-1003.
30. Recent calculations reported by Kaneti suggest a concerted, though seemingly asynchronous, addition between the imine and the monoenol isomer of the anhydride. See: Kaneti, J.; Bakalova, S. M.; Pojarlieff, I. G. J. Org. Chem. 2003, 68, 6824-6827. Given the enormous temperature differences for the reactions of various anhydrides with imines (-60 °C for homophthalic anhydride, 160 °C for succinic anhydride) it may be difficult to propose an accurate and still unified mechanism for these reactions. The acylative mechanism is consistent with our findings with regard to electronic influences and is not wholly inconsistent with the hypotheses of Kaneti.
31. Prepared by alkylation of the corresponding arylacetic esters with an α-chloroacetic ester. See Supporting Information.
32. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428.
33. Yamada, K.; Kubo, T.; Tokuyama, H.; Fukuyama, T. Synlett 2002, 231-234.
34. The chemistry described in this report was used in conjunction with a related sequence, which produces fused and spirocyclic δ-lactams, and these experiments will be reported shortly. A complete description of the library of 570 structurally diverse products along with preliminary screening results will be described in a full account of this work.