Potentially biomimetic total synthesis and relative stereochemical assignment of (±)-gracilamine

Angewandte Chemie - International Edition

Volumn 51, Issue 40, 2012, Pages 10141-10144

  Tian, Songchuan ^a   Zi, Weiwei ^a   Ma, Dawei ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

alkaloids; cycloaddition; fused ring systems; natural products; total synthesis

Indexed keywords

ALKALOIDS; BIOCHEMISTRY; CYCLOADDITION; REACTION INTERMEDIATES; SYNTHESIS (CHEMICAL);

BIOSYNTHESIS PATHWAYS; DEBENZYLATION; FIVE-MEMBERED RINGS; FUSED-RING SYSTEM; NATURAL PRODUCTS; TOTAL SYNTHESIS; [3+2]-CYCLOADDITION;

BIOMIMETIC PROCESSES;

EID: 84866976183     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201205711     Document Type: Article

References (44)

1. M. Kitajima, H. Takayama, Top. Curr. Chem. 2012, 309, 1
2. Z. Jin, Nat. Prod. Rep. 2007, 24, 886
3. N. Unver, Phytochem. Rev. 2007, 6, 125
4. Z. Jin, Nat. Prod. Rep. 2005, 22, 111.
5. J. Marco-Contelles, M. C. Carreiras, C. Rodríguez, M. Villarroya, A. G. García, Chem. Rev. 2006, 106, 116
6. B. Küenburg, L. Czollner, J. Fröhlich, U. Jordis, Org. Process Res. Dev. 1999, 3, 425
7. S. Kodama, Y. Hamashima, K. Nishide, M. Node, Angew. Chem. 2004, 116, 2713
8. Angew. Chem. Int. Ed. 2004, 43, 2659
9. B. M. Trost, W. Tang, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 14785
10. X.-D. Hu, Y. Tu, E. Zhang, S. Gao, S. Wang, A. Wang, C. Fan, M. Wang, Org. Lett. 2006, 8, 1823
11. V. Satcharoen, N. J. McLean, S. C. Kemp, N. P. Camp, R. C. D. Brown, Org. Lett. 2007, 9, 1867
12. T. Ishikawa, K. Kudo, K. Kuroyabu, S. Uchida, T. Kudoh, S. Saito, J. Org. Chem. 2008, 73, 7498
13. P. Magnus, N. Sane, B. P. Fauber, V. Lynch, J. Am. Chem. Soc. 2009, 131, 16045.
14. A. G. Schultz, M. A. Holoboski, M. S. Smyth, J. Am. Chem. Soc. 1996, 118, 6210
15. A. Padwa, M. A. Bradney, S. M. Lynch, J. Org. Chem. 2001, 66, 1716
16. M. Matveenko, O. J. Kokas, M. G. Banwell, A. C. Willis, Org. Lett. 2007, 9, 3683
17. K. Yamada, M. Yamashita, T. Sumiyoshi, K. Nishimura, K. Tomioka, Org. Lett. 2009, 11, 1631
18. C. Girõ Mañas, V. L. Paddock, C. G. Bochet, A. C. Spivey, A. J. P. White, I. Mann, W. Oppolzer, J. Am. Chem. Soc. 2010, 132, 5176.
19. I. R. Baxendale, S. V. Ley, C. Piutti, Angew. Chem. 2002, 114, 2298
20. Angew. Chem. Int. Ed. 2002, 41, 2194.
21. Y. Tsuda, A. Ukai, K. Isobe, Tetrahedron Lett. 1972, 13, 3153
22. J. B. Hendrickson, T. L. Bogard, M. E. Fisch, S. Grossert, N. Yoshimur, J. Am. Chem. Soc. 1974, 96, 7781
23. S. Danishefsky, J. Morris, G. Mullen, R. Gammill, J. Am. Chem. Soc. 1980, 102, 2838
24. M. N. Abelman, L. E. Overman, V. D. Tran, J. Am. Chem. Soc. 1990, 112, 6959
25. J. H. Rigby, A. Cavezza, M. J. Heeg, J. Am. Chem. Soc. 1998, 120, 3664
26. S. W. Baldwin, J. S. Debenham, Org. Lett. 2000, 2, 99
27. F. M. Zhang, Y. Q. Tu, J. D. Liu, X. H. Fan, L. Shi, X. D. Hu, S. H. Wang, Y. Q. Zhang, Tetrahedron 2006, 62, 9446.
28. A. Evidente, A. Kornienko, Phytochem. Rev. 2009, 8, 449.
29. N. Ünver, G. Ä°. Kaya, Turk. J. Chem. 2005, 29, 547.
30. L. Petit, M. G. Banwell, A. C. Willis, Org. Lett. 2011, 13, 5800
31. G. Pandey, N. R. Gupta, S. R. Gadre, Eur. J. Org. Chem. 2011, 740.
32. S. Kodama, H. Takita, T. Kajimoto, K. Nishide, M. Node, Tetrahedron 2004, 60, 4901.
33. H. Kapnang, G. Charles, Tetrahedron Lett. 1983, 24, 3233.
34. CCDC 889289, 889290, 889291, and 889292 (15, 16 a, 27, and gracilamine) contain 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.
35. W. H. Pearson, F. E. Lovering, J. Org. Chem. 1998, 63, 3607
36. A. K. Machocho, J. Bastida, C. Codina, F. Viladomat, R. Brun, S. C. Chhabra, Phytochemistry 2004, 65, 3143.
37. A. G. González, G. Delafuente, M. Reina, I. Timon, Heterocycles 1984, 22, 667.
38. D. A. Barr, R. Grigg, H. Q. N. Gunaratne, J. Kemp, P. McMeekin, V. Sridharan, Tetrahedron 1988, 44, 557
39. K. Amornraksa, D. Barr, G. Donegan, R. Grigg, P. Ratananukul, V. Sridharan, Tetrahedron 1989, 45, 4649.
40. C. Chen, X. Li, S. L. Schreiber, J. Am. Chem. Soc. 2003, 125, 10174
41. A. Zubia, L. Mendoza, S. Vivanco, E. Aldaba, T. Carrascal, B. Lecea, A. Arrieta, T. Zimmerman, F. Vidal-Vanaclocha, F. P. Cossío, Angew. Chem. 2005, 117, 2963
42. Angew. Chem. Int. Ed. 2005, 44, 2903
43. R. Stohler, F. Wahl, A. Pfaltz, Synthesis 2005, 1431
44. C.-J. Wang, G. Liang, Z.-Y. Xue, F. Gao, J. Am. Chem. Soc. 2008, 130, 17250.