Transition metals in organic synthesis, part 97: 1 Silver-catalyzed synthesis of hexahalogenated 2,2′-bipyrroles

Synlett

Volumn , Issue 19, 2011, Pages 2795-2798

  Martin, René ^a   Jäger, Anne ^a   Knölker, Hans Joachim ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

alkaloids; catalysis; cyclization; halogenation; pyrroles

Indexed keywords

1,1' DIMETHYL 2,2' BIPYRROLE; 2,3 DIHYDRO 1' METHYL 1 TOSYL 2,2' BIPYRROLE; ACETYLENE; BIPYRROLE; HEXAHALOGENATED 1,1' DIMETHYL 2,2' BIPYRROLE DERIVATIVE; PYRROLE DERIVATIVE; PYRROLINE; SILVER; TOLUENESULFONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; MOLECULAR INTERACTION; ORGANIC CHEMISTRY; SYNTHESIS;

EID: 81855178224     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1289563     Document Type: Article

References (43)

1. For Part 96, see:, Thomas C, Kataeva O, Knölker H.-J, Synlett 2011 2663
2. See for example:, Fan H, Peng J, Hamann M T., Hu J.-F, Chem. Rev. 2008 108 264
3. Fukuda T, Ishibashi F, Iwao M, Heterocycles 2011 83 491
4. Gribble G W., In Comprehensive Heterocyclic Chemistry II Vol. 2 Katritzky A R. Rees C W. Scriven E F. V. Elsevier Oxford 1996 207
5. For recent work, see:, Bellur E, Langer P, Tetrahedron Lett. 2006 47 2151
6. Morita N, Krause N, Eur. J. Org. Chem. 2006 4634
7. Knight D W., Rost H C., Sharland C M., Singkhonrat J, Tetrahedron Lett. 2007 48 7906
8. Bergner I, Opatz T, J. Org. Chem. 2007 72 7083
9. Liu W, Jiang H, Huang L, Org. Lett. 2010 12 312; and references cited therein
10. Agarwal S, Knölker H.-J, Org. Biomol. Chem. 2004 2 3060
11. For a review, see:, Agarwal S, Cämmerer S, Filali S, Fröhner W, Knöll J, Krahl M P., Reddy K R., Knölker H.-J, Curr. Org. Chem. 2005 9 1601
12. Knölker H.-J, Agarwal S, Synlett 2004 1767
13. Knölker H.-J, Agarwal S, Tetrahedron Lett. 2005 46 1173
14. Martin R, Jäger A, Böhl M, Richter S, Fedorov R, Manstein D J., Gutzeit H O., Knölker H.-J, Angew. Chem. Int. Ed. 2009 48 8042; Angew. Chem. 2009, 121, 8186
15. For a review, see:, Forke R, Gruner K K., Knott K E., Auschill S, Agarwal S, Martin R, Böhl M, Richter S, Tsiavaliaris G, Fedorov R, Manstein D J., Gutzeit H O., Knölker H.-J, Pure Appl. Chem. 2010 82 1975
16. Fedorov R, Böhl M, Tsiavaliaris G, Hartmann F K., Taft M H., Baruch P, Brenner B, Martin R, Knölker H.-J, Gutzeit H O., Manstein D J., Nat. Struct. Mol. Biol. 2009 16 80
17. Martin R, Kirst J, Weidlich S, Schieb H, Schlechtingen G, Jäger A, Rajendran L, Böhl M, Richter S, Fedorov R, Manstein D J., Gutzeit H O., Klafki H, Wiltfang J, Simons K, Knölker H.-J, Med. Chem. Res. 2010 19 S23
18. Martin R, Agarwal S, Jäger A, Böhl M, Richter S, Tsiavaliaris G, Fedorov R, Manstein D J., Gutzeit H O., Knölker H.-J, In The Chemistry and Biological Activity of Synthetic and Natural Compounds, Modern Aspects of Chemistry of Heterocycles Kartsev V G. ICSPF Press Moscow 2010 110
19. Preller M, Chinthalapudi K, Martin R, Knölker H.-J, Manstein D J., J. Med. Chem. 2011 54 3675
20. Chintalapudi K, Taft M H., Martin R, Heissler S M., Preller M, Hartmann F K., Brandstaetter H, Kendrick-Jones J, Tsiavaliaris G, Gutzeit H O., Fedorov R, Buss F, Knölker H.-J, Coluccio L M., Manstein D J., J. Biol. Chem. 2011 286 29700
21. Andersen R J., Wolfe M S., Faulkner D J., Mar. Biol. 1974 27 281
22. Tittlemier S A., Simon M, Jarman W M., Elliott J E., Norstrom R J., Environ. Sci. Technol. 1999 33 26
23. Gribble G W., Blank D H., Jasinski J P., Chem. Commun. 1999 2195
24. Blank D H., Gribble G W., Schneekloth J S., Jasinski J P., J. Chem. Cryst. 2002 32 541
25. Fu L, Gribble G W., Tetrahedron Lett. 2008 49 7352
26. Bennett J W., Bentley R, Adv. App. Microbiol. 2000 47 1
27. Fürstner A, Angew. Chem. Int. Ed. 2003 42 3582; Angew. Chem. 2003, 115, 3706
28. Laatsch H, Kellner M, Weyland H, J. Antibiot. 1991 44 187
29. Carté B, Faulkner D J., J. Org. Chem. 1983 48 2314
30. Lindquist N, Fenical W, Experientia 1991 47 504
31. Blackman A J., Li C, Aust. J. Chem. 1994 47 1625
32. Flögel O, Reissig H.-U, Synlett 2004 895
33. Matsumoto S, Kobayashi T, Ogura K, Heterocycles 2005 66 319
34. Dohi T, Morimoto K, Maruyama A, Kita Y, Org. Lett. 2006 8 2007
35. Jolicoeur B, Lubell W D., Org. Lett. 2006 8 6107
36. Jiao L, Hao E, Vicente G H., Smith K M., J. Org. Chem. 2007 72 8119; and references cited therein
37. Love B E., Raje P S., Williams II T C., Synlett 1994 493
38. Kawate T, Nakagawa M, Yamazaki H, Hirayama M, Hino T, Chem. Pharm. Bull. 1993 41 287
39. Sisko J, Weinreb S M., J. Org. Chem. 1990 55 393
40. Kauffmann T, Lexy H, Chem. Ber. 1981 114 3674
41. Dohi T, Morimoto K, Ito M, Kita Y, Synthesis 2007 2913
42. Sánchez-García D, Borrell J I., Nonell S, Org. Lett. 2009 11 77
43. Rosenfelder N, Ostrowicz P, Fu L, Gribble G W., Tittlemier S A., Fey W, Vetter W, J. Chromatogr. A 2010 1217 2050