Asymmetric bromine-lithium exchange: Application toward the synthesis of natural product

Organic Letters

Volumn 15, Issue 16, 2013, Pages 4270-4273

  Graff, Julien ^a   Debande, Thibaut ^a   Praz, Jézabel ^a   Guénée, Laure ^a   Alexakis, Alexandre ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; BROMINE; COUMARIN DERIVATIVE; ISOKOTANIN A; LITHIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BIOLOGICAL PRODUCTS; BROMINE; CATALYSIS; COUMARINS; LITHIUM; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84882768334     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4021157     Document Type: Article

References (44)

1. Bringmann, G.; Mortimer, A. J. P.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breunig, M. Angew. Chem., Int. Ed. 2005, 44, 5384-5427
2. Fan, C.-A.; Ferber, B.; Kagan, H. B.; Lafon, O.; Lesot, P. Tetrahedron: Asymmetry 2008, 19, 2666-2677
3. Perron, Q.; Praz, J.; Alexakis, A. Tetrahedron: Asymmetry 2009, 20, 1004-1007
4. Perron, Q.; Alexakis, A. Adv. Synth. Catal. 2010, 352, 2611-2620
5. Praz, J.; Guénée, L.; Aziz, S.; Berkessel, A.; Alexakis, A. Adv. Synth. Catal. 2012, 354, 1780-1790
6. Bringmann, G.; Gulder, T.; Gulder, T. A. M.; Breuning, M. Chem. Rev. 2011, 111, 563-639 and references cited therein
7. McCormick, M. H.; Stark, W. M.; Pittenger, G. E.; Pittenger, R. C.; McGuire, J. M. Antibiot. Annu. 1955, 56, 606
8. Bringmann, G.; Menche, D.; Kraus, J.; Mühlbacher, J.; Peters, K.; Peters, E.-M.; Brun, R.; Bezabih, M.; Abegaz, B. M. J. Org. Chem. 2002, 67, 5595-5610
9. Bringmann, G.; Menche, D. Angew. Chem., Int. Ed. 2001, 40, 1687-1690
10. Groh, M.; Meidlinger, D.; Bringmann, G.; Speicher, A. Org. Lett. 2012, 14, 4548-4551
11. Broka, C. A. Tetrahedron Lett. 1991, 32 (7) 859-862
12. Tanaka, M.; Mukaiyama, C.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. J. Org. Chem. 1995, 60, 4339-4352
13. Bringmann, G.; Hinrichs, J.; Henschel, P.; Kraus, J.; Peters, K.; Peters, E.-M. Eur. J. Org. Chem. 2002, 1096-1106
14. Hussain, H.; Hussain, J.; Al-Harrasi, A.; Krohn, K. Tetrahedron 2012, 68, 2553-2578
15. Hüttel, W.; Nieger, M.; Müller, M. Synthesis 2003, 12, 1803-1808
16. Kozolwski, M. C.; Morgan, B. J.; Linton, E. C. Chem. Soc. Rev. 2009, 38, 3193-3207
17. Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655-2658
18. Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2577-2580
19. Meyers, A. I.; Willemsen, J. J. Tetrahedron 1998, 54, 10493-10511
20. Lipshutz, B. H.; Kayser, F.; Liu, Z.-P. Angew. Chem., Int. Ed. Engl. 1994, 33, 1842-1844 and references cited therein
21. Li, X.; Hewgley, J. B.; Mulrooney, C. A.; Yang, J.; Kozolwski, M. C. J. Org. Chem. 2003, 68, 5500-5511
22. Li, X.; Yang, J.; Kozolwski, M. C. Org. Lett. 2001, 3, 1137-1140
23. Laakso, J. A.; Narske, E. D.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. J. Nat. Prod. 1994, 57, 128
24. Lin, G.-Q.; Zhong, M. Tetrahedron Lett. 1996, 37, 3015-3018
25. Dabrowski, M.; Kubicka, J.; Luliński, S.; Serwatowski, J. Tetrahedron Lett. 2005, 46, 4175-4178
26. Snieckus, V. Chem. Rev. 1990, 90, 879-933
27. Bo, Z.; Schlüter, A. D. J. Org. Chem. 2002, 67, 5327-5332
28. Rehm, J. D. D.; Ziemer, B.; Szeimies, G. Eur. J. Org. Chem. 1999, 2079-2085
29. Leroux, F. R.; Simon, R.; Nicod, N. Lett. Org. Chem 2006, 3, 948-954
30. Diemer, V.; Leroux, F. R.; Colobert, F. Eur. J. Org. Chem. 2011, 327-340
31. Alexakis, A.; Aujard, I.; Kanger, T.; Mangeney, P. Organic Syntheses, Coll. Vol. 10, p 312; Vol. 76, p 23.
32. Cuvinot, D.; Mangeney, P.; Alexakis, A.; Normant, J.-F. J. Org. Chem. 1989, 54, 2420-2425
33. Rauniyar, V.; Zhai, H.; Hall, D. G. J. Am. Chem. Soc. 2008, 130, 8481-8490
34. Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1989, 111, 8266-8268
35. Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429-4438
36. Mizuno, M.; Kanai, M.; Iiada, A.; Tomioka, K. Tetrahedron 1997, 53, 10699-10708
37. Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron: Asymmetry 1995, 6, 2527-2533
38. Haalten, H. L.; van Koten, G.; Grove, D. M.; Kuilman, T.; Piekstra, O. G.; Hulshof, L. A.; Sheldon, R. A Tetrahedron 1989, 45 (17) 5565-5578
39. Capdevielle, P.; Maumy, M. Tetrahedron Lett. 1993, 34 (6) 1007-1010
40. CCDC-953058 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.
41. Büchi, G.; Klaubrt, D. H.; Schank, R. C.; Weinreb, S. M.; Wogan, G. N. J. Org. Chem. 1971, 36, 1143-1147
42. For the first racemic synthesis of kotanin, see: Büchi, G.; Luk, K. C.; Kobbe, B.; Townsend, J. M. J. Org. Chem. 1977, 42, 244-246
43. Lin, G.-Q.; Zhong, M. Tetrahedron: Asymmetry 1997, 9, 1369-1372
44. Lanfranchi, D. A.; Hanquet, G. J. Org. Chem. 2006, 71, 4854-4861