Extending pummerer reaction chemistry: Application to the assembly of the pentacyclic core of dibromopalau'amine

Organic Letters

Volumn 12, Issue 20, 2010, Pages 4532-4535

  Feldman, Ken S ^a   Nuriye, Ahmed Yimam ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; GUANIDINE DERIVATIVE; PALAU'AMINE; SPIRO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

BROMINE COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; GUANIDINES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 77957826986     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1018322     Document Type: Article

References (37)

1. Kinnel, R. B.; Gehrken, H.-P.; Scheuer, P. J. J. Am. Chem. Soc. 1993, 115, 3376-3377
2. Kinnel, R. B.; Gehrken, H.-P.; Swali, R.; Skoropowski, G.; Scheuer, P. J. J. Org. Chem. 1998, 63, 3281-3286
3. Grube, A.; Köck, M. Angew. Chem., Int. Ed. 2007, 46, 2320-2324
4. Buchanan, M. S.; Carroll, A. R.; Quinn, R. J. Tetrahedron Lett. 2007, 48, 4573-4574
5. Köck, M.; Grube, A.; Seiple, I. B.; Baran, P. S. Angew. Chem., Int. Ed. 2007, 46, 6586-6594
6. Lanman, B. A.; Overman, L. E.; Paulini, R.; White, N. S. J. Am. Chem. Soc. 2007, 129, 12896-12900
7. Overman, L. E.; Rodgers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Am. Chem. Soc. 1997, 119, 7159-7160
8. Dilley, A. S.; Romo, D. Org. Lett. 2001, 3, 1535-1538
9. Bélanger, G.; Hong, F.-T.; Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Org. Chem. 2002, 67, 7880-7883
10. Katz, J. D.; Overman, L. E. Tetrahedron 2004, 60, 9559-9568
11. Lovely, C. J.; Du, H.; He, Y.; Rasika Das, H. V. Org. Lett. 2004, 6, 735-738
12. Garrido-Hernandez, H.; Nakadai, M.; Vimolratana, M.; Li, Q.; Doundoulakis, T.; Harran, P. G. Angew. Chem., Int. Ed. 2005, 44, 765-769
13. Dransfield, P. J.; Dilley, A. S.; Wang, S.; Romo, D. Tetrahedron 2006, 62, 5223-5247
14. Tan, X.; Chen, C. Angew. Chem., Int. Ed. 2006, 45, 4345-4348
15. Lanman, B. A.; Overman, L. E. Heterocycles 2006, 70, 557-570
16. Bultman, M. S.; Ma, J.; Gin., D. Y. Angew. Chem., Int. Ed. 2008, 47, 6821-6824
17. Zancanella, M. A.; Romo, D. Org. Lett. 2008, 10, 3685-3688
18. Hudon, J.; Cernak, T. A.; Ashenhurst, J. A.; Gleason, J. L. Angew. Chem., Int. Ed. 2008, 47, 8885-8888
19. Li, Q.; Hurley, P.; Ding, H.; Roberts, A. G.; Akella, R.; Harran, P. G. J. Org. Chem. 2009, 74, 5909-5919
20. Seiple, I. B.; Su, S.; Young, I. S.; Lewis, C. A.; Yamaguchi, J.; Baran, P. S. Angew. Chem., Int. Ed. 2010, 49, 1095-1098
21. Al-Mourabit, A.; Potier, P. Eur. J. Org. Chem. 2001, 237-243
22. Büchi, G.; Foley, L. H. J. Am. Chem. Soc. 1982, 104, 1776-1777
23. Wiese, K. J.; Yakushijin, K.; Horne, D. A. Tetrahedron Lett. 2002, 43, 5135-5136
24. Feldman, K. S.; Skoumbourdis, A. P. Org. Lett. 2005, 7, 929-931
25. Feldman, K. S.; Skoumbourdis, A. P.; Fodor, M. D. J. Org. Chem. 2007, 72, 8076-8086
26. Lu, J.; Tan, X.; Chen, C. J. Am. Chem. Soc. 2007, 129, 7768-7769
27. Feldman, K. S.; Fodor, M. D. J. Am. Chem. Soc. 2008, 130, 14964-14965
28. Feldman, K. S.; Fodor, M. D. J. Org. Chem. 2009, 74, 3449-3461
29. Feldman, K. S. Tetrahedron 2006, 62, 5003-5034
30. Feldman, K. S.; Fodor, M. D.; Skoumbourdis, A. P. Synthesis 2009, 3162-3173
31. Li, J. M. S. Thesis, Pennsylvania State University, 2009.
32. Vollinga, R. C.; Menge, W. M. P. B.; Timmerman, H. Recl. Trav. Pays-Bas 1993, 112, 123-125
33. For a related Diels - Alder reaction of a β-imidazole unsaturated ester, see: Kawasaki, I.; Sakaguchi, N.; Khadeer, A.; Yamashita, M.; Ohta, S. Tetrahedron 2006, 62, 10182-10192
34. Zhdankin, V. V.; Crittell, C. M.; Stang, P. J.; Zefirov, N. S. Tetrahedron Lett. 1990, 31, 4821-4824
35. Cambridge Crystallographic Data Centre deposition number: CCDC 782151. The data can be obtained free from Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data-request/cif.
36. Kirmse, W. Carbene Chemistry; Academic Press: New York, NY, 1971; pp 484 - 487.
37. Danheiser, R. L.; Miller, R. F.; Brisbois, R. G.; Park, S. Z. J. Org. Chem. 1990, 55, 1959-1964