Cu/Mn Co-oxidized cyclization for the synthesis of highly substituted pyrrole derivatives from amino acid esters: A strategy for the biomimetic syntheses of lycogarubin c and chromopyrrolic acid

Journal of Organic Chemistry

Volumn 79, Issue 13, 2014, Pages 6061-6068

  Zhou, Nini ^a   Xie, Tao ^a   Liu, Lin ^a   Xie, Zhixiang ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BIOMIMETICS; ESTERIFICATION; ESTERS; POTASSIUM COMPOUNDS;

AMINO ACID ESTERS; BIOMIMETIC SYNTHESIS; CHROMOPYRROLIC ACID; ELECTRON WITHDRAWING GROUP; ELECTRON-DONATING; NATURAL PRODUCTS; OXIDATIVE CYCLIZATION; PYRROLE DERIVATIVES;

CYCLIZATION;

AMINO ACID DERIVATIVE; COPPER; ESTER DERIVATIVE; LYCOGARUBIN C; MANGANESE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG; AMINO ACID; CHROMOPYRROLIC ACID; ESTER; INDOLE DERIVATIVE;

ARTICLE; BIOMIMETICS; BIOSYNTHESIS; CHEMICAL STRUCTURE; CYCLIZATION; DEAMINATION; ELECTRON TRANSPORT; OXIDATION; OXIDATIVE DEHYDROGENATION; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS; X RAY CRYSTALLOGRAPHY; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION;

AMINO ACIDS; BIOMIMETICS; CATALYSIS; COPPER; CYCLIZATION; ESTERS; INDOLES; MANGANESE; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PYRROLES;

EID: 84903742791     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500740w     Document Type: Article

References (52)

1. Fan, H.; Peng, J. N.; Hamann, M. T.; Hu, J.-F. Chem. Rev. 2008, 108, 264-287
2. Young, I. S.; Thorntonb, P. D.; Thompson, A. Nat. Prod. Rep. 2010, 27, 1801-1839
3. Al-Mourabit, A.; Zancanella, M. A.; Tilvic, S.; Romo, D. Nat. Prod. Rep. 2011, 28, 1229-1260
4. Heugebaert, T. S. A.; Roman, B. L.; Stevens, C. V. Chem. Soc. Rev. 2012, 41, 5626-5640
5. Kathirav, M. K.; Salake, A. B.; Chothe, A. S.; Dudhe, P. B.; Watode, R. P.; Mukta, M. S.; Gadhwe, S. Bioorg. Med. Chem. 2012, 20, 5678-5698
6. Su, T.-L.; Lee, T.-C.; Kakadiya, R. Eur. J. Med. Chem. 2013, 69, 609-621
7. Black, D. S. Sci. Synth. 2001, 9 (13) 441-535
8. Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075
9. Kamijo, S.; Kanazawa, C.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 9260-9266
10. Bergman, J.; Janosik, T. 3.03-Pyrroles and their Benzo Derivatives: Synthesis. In Comprehensive Heterocyclic Chemistry III; Elsevier: New York, 2008; Vol. 3, p 269-351.
11. Yasui, E.; Wada, M.; Takamura, N. Tetrahedron Lett. 2009, 50, 4762-4765
12. Mizuno, A.; Kusama, H.; Iwasawa, N. Angew. Chem., Int. Ed. 2009, 48, 8318-8320
13. Ciez, D. Org. Lett. 2009, 11, 4282-4285
14. Lourdusamy, E.; Yao, L.; Park, C.-M. Angew. Chem., Int. Ed. 2010, 49, 7963-7967
15. Li, Q. J.; Fan, A. L.; Z. Lu, Y.; Cui, Y. X.; Lin, W. H.; Jia, Y. X. Org. Lett. 2010, 12, 4066-4069
16. Xin, X.; Wang, D.; Li, X.; Wan, B. Angew. Chem., Int. Ed. 2012, 51, 1693-1697
17. Jiang, Y.; Chan, W. C.; Park, C.-M. J. Am. Chem. Soc. 2012, 134, 4104-4107
18. Humenny, W. J.; Kyriacou, P.; Sapeta, K.; Karadeolian, A.; Kerr, M. A. Angew. Chem., Int. Ed. 2012, 51, 11088-11091
19. Schultz, E. E.; Sarpong, R. J. Am. Chem. Soc. 2013, 135, 4696-4699
20. Parr, B. T.; Green, S. A.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 4716-4718
21. Zhang, M.; Fang, X.; Neumann, H.; Beller, M. J. Am. Chem. Soc. 2013, 135, 11384-11388
22. Alford, J. S.; Spangler, J. E.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 11712-11715
23. Michlik, S.; Kempe, R. Nat. Chem. 2013, 5, 140-144
24. Lian, Y.; Huber, T.; Hesp, K. D.; Bergman, R. G.; Ellman, J. A. Angew. Chem., Int. Ed. 2013, 52, 629-633
25. Srimani, D.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2013, 52, 4012-4015
26. Nishizawa, T.; Gruschow, S.; Jayamaha, D.-H. E.; Nishizawa-Haraha, C.; Sherman, D. H. J. Am. Chem. Soc. 2006, 128, 724-725
27. Frode, R.; Hinze, C.; Josten, I.; Schmidt, B.; Steffan, B.; Steglich, W. Tetrahedron Lett. 1994, 35, 1689-1690
28. Hashimoto, T.; Yasuda, A.; Akazawa, K.; Takaoka, S.; Tori, M.; Akazawa, Y. Tetrahedron Lett. 1994, 35, 2559-2560
29. Razzak, M.; Brabander, J. D. Nat. Chem. Biol. 2011, 7, 865-875
30. Gravel, E.; Poupon, E. Nat. Prod. Rep. 2010, 27, 32-56
31. Lautu, S.; Song, L.; Demange, L.; Lombes, T.; Galons, H.; Challis, G. L.; Pemodet, J.-L. Angew. Chem., Int. Ed. 2012, 51, 7454-7458
32. Bulger, P. G.; Bagal, S. K.; Marquez, R. Nat. Prod. Rep. 2008, 25, 254-297
33. Beaudry, C. M.; Malerich, J. P.; Trauner, D. Chem. Rev. 2005, 105, 4757-4778
34. Yasui, E.; Wada, M.; Takamura, N. Tetrahedron Lett. 2009, 50, 4762-4765
35. CCDC 969628 (5a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
36. Al-Hmoud, L.; Jones, C. W. J. Catal. 2013, 301, 116-124
37. Zhu, B. L.; Lazar, M.; Trewyn, B. G.; Angelici, R. J. J. Catal. 2008, 260, 1-6
38. Koch, D.; Schäfer, H. Angew. Chem., Int. Ed. 1973, 12, 245-246
39. Khetan, S. K. Chem. Commun. 1972, 917-917
40. Herten, B. W.; Poulton, G. A. Chem. Commun. 1975, 456-457
41. Carr, R. M.; Norman, R. O. C.; Vernon, J. M. Chem. Commun. 1977, 854-855
42. Carr, R. M.; Norman, R. O. C.; Vernon, J. M. J. Chem. Soc., Perkin Trans. 1 1980, 156-162
43. Sukari, M. A.; Vernon, J. M. Tetrahedron 1983, 39, 793-796
44. Tsai, A.; Chuang, C.-P. Tetrahedron 2006, 62, 2235-2239
45. Wang, J.-Y.; Liu, S.-P.; Yu, W. Synlett 2009, 2529-2533
46. Snider, B. B.; Kwon, T. J. Org. Chem. 1990, 55, 1965-1968
47. Yin, J.; Wang, C.; Kong, L. L.; Cai, S. J.; Gao, S. H. Angew. Chem., Int. Ed. 2012, 51, 7786-7789
48. Knolker, H.-J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303-4428
49. Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373-6380
50. Hinze, C.; Kreipl, A.; Terpin, A.; Steglich, W. Synthesis 2007, 4, 608-612
51. Fu, L. F.; Gribble, G. W. Tetrahedron Lett. 2010, 51, 537-539
52. Oakdale, J. S.; Boger, D. L. Org. Lett. 2010, 12, 1132-1134