Oxidative carbon-carbon bond formation in the synthesis of bioactive spiro β-lactams

Organic Letters

Volumn 11, Issue 13, 2009, Pages 2820-2823

  Liang, Jixuan ^a   Chen, Jingbo ^a   Du, Fengxiang ^a   Zeng, Xianghui ^a   Li, Ang ^a   Zhang, Hongbin ^a  

^a YUNNAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; 4 AMINOPHENOL; 4-AMINOPHENOL; AMINOPHENOL DERIVATIVE; BETA LACTAM; INDOLE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMINOPHENOLS; BETA-LACTAMS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; INDOLES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PYRROLIDINONES; SPIRO COMPOUNDS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 67649496359     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901005x     Document Type: Article

References (35)

1. For reviews on synthesis and application of β-lactams, see: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Rev. 2007, 107, 4437.
2. (b) France, S.; Weatherwax, A.; Taggi, A. E.; Lectka, T. Acc. Chem. Res. 2004, 37, 594.
3. (c) Singh, G. S. Tetrahedron 2003, 59, 7631.
4. Butler, M. S. Nat. Prod. Rep. 2005, 22, 162.
5. (a) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Heterocycles 2003, 53, 149.
6. (b) Wardrop, D. J.; Burge, M. S. J. Org. Chem. 2005, 70, 10271.
7. (c) Dohi, T.; Maruyama, A.; Minamitsuji, Y.; Takenaga, N.; Kita, Y. Chem. Cmmun. 2007, 1224.
8. For recent reviews on oxidative coupling, see: (a) Quideau, S.; Pouysegu, L.; Deffieux, D. Synlett 2008, 467.
9. (b) Ciufolini, M. A.; Braun, N. A.; Canesi, S.; Ousmer, M.; Chang, J.; Chai, D. Synthesis 2007, 3759.
10. (c) Magdziak, D.; Meek, S. J.; Pettus, T. R. R. Chem. Rev. 2004, 104, 1383.
11. (d) Rodrigues, S.; Wipf, P. Synthesis 2004, 2767.
12. (e) Van De Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367.
13. For reviews on polyvalent iodine chemistry, see: (a) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299.
14. (b) Richardson, R. D.; Wirth, T. Angew. Chem., Int. Ed. 2006, 45, 4402.
15. (c) Wirth, T. Angew. Chem., Int. Ed. 2005, 44, 3656.
16. (d) Moriarty, R. M. J. Org. Chem. 2005, 70, 2893.
17. (e) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523, and references cited therein.
18. Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054.
19. The bioassay was carried out with the MTT method. In vitro studies demonstrated that the azetidinones listed in Table 2are active against A431, HepG-2 and Skov-3 tumor cells.
20. (a) Peng, H. M.; Wester, R. D. J. Org. Chem. 2008, 73, 2.169.
21. (b) Eickhoff, H.; Jung, G.; Rieker, A. Tetrahedron 2001, 57, 353, references cited therein.
22. Baran, P. S.; DeMartino, M. P. Angew. Chem., Int. Ed. 2006, 45, 7083.
23. For recent synthesis of oxindoles, see: (a) Felpin, F.-X.; Ibarguren, O.; Nassar-Hardy, L.; Fouquet, E. J. Org. Chem. 2009, 74, 1349.
24. (b) Luan, X.; Mariz, R.; Robert, C.; Gatti, M.; Blumentritt, S.; Linden, A.; Dorta, R. Org. Lett. 2008, 10, 5569.
25. (c) Shanmugam, P.; Vaithiyanathan, V. tetrahedron 2008, 64, 3322.
26. (d) Hillgren, J. M.; Marsden, S. P. J. Org. Chem. 2008, 73, 6459.
27. (e) Kündig, E. P.; Seidel, T. M.; Jia, Y.-X.; Bernardinelli, G. Angew. Chem., Int. Ed. 2007, 46, 8484.
28. (f) Teichert, A.; Jantos, K.; Harms, K.; Studer, A. Org. Lett. 2004, 6, 3477, and references cited thereinFor recent synthesis of oxindoles with an oxidative dearomatization strategy, see:
29. (g) Pouységu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425.
30. (h) Quideau, S.; Pouységu, L.; Avellan, A.-V.; Whelligan, D. K.; Looney, M. A. Tetrahedron Lett. 2001, 42, 7393.
31. In the literature, Quideau and Clive had elegantly demonstrated the synthesis of 2,3-dihydroindoles with an oxidative dearomatization strategy, see:(a) Quideau, S.; Pouységu, L.; Oxoby, M.; Looney, M. A. Tetrahedron 2001, 57, 319.
32. (b) Fletcher, S. P.; Clive, D. L. J.; Peng, J.; Wingert, D. A. Org. Lett. 2005, 7, 23.
33. Trost, B. M.; Brennan, M. K. Org. Lett. 2006, 8, 2027.
34. Formation of spirolactams by oxidative carbon-nitrogen bond coupling had been, elegantly demonstrated by ref 3 and: (a) Ousmer, M.; Braun, N. A.; Bavoux, C.; Perrin, M.; Ciufolini, M. A. J. Am. Chem. Soc. 2001, 123, 7534, and references cites therein.
35. (b) Ousmer, M.; Braun, N. A.; Ciufolini, M. A. Org. Lett. 2001, 3, 765, and references cites therein.