Gold(I)-catalyzed formation of bridged and fused carbocycles

Pure and Applied Chemistry

Volumn 85, Issue 6, 2013, Pages 1161-1173

  Barabé, Francis ^a   Levesque, Patrick ^a   Sow, Boubacar ^a   Bellavance, Gabriel ^a   Bétournay, Geneviève ^a   Barriault, Louis ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

Alkynes; Carbocycles; Catalysis; Cyclizations; Cycloadditions; Gold

Indexed keywords

ALKYNES; CARBOCYCLES; CO-ORDINATION CHEMISTRIES; CYCLIZATIONS; CYCLOADDITIONS; HOMOGENEOUS CATALYSIS; ORGANIC TRANSFORMATIONS; SCIENTIFIC COMMUNITY;

CATALYSIS; COORDINATION REACTIONS; GOLD; KETONES; PHOSPHORUS COMPOUNDS; REACTION KINETICS;

CYCLIZATION;

EID: 84878881186     PISSN: 00334545     EISSN: 13653075     Source Type: Journal    
DOI: 10.1351/PAC-CON-13-01-02     Document Type: Article

References (53)

1. F. D. Toste, D. J. Gorin. Nature 446, 395 (2007).
2. For recent reviews, see: (a) E. Jiménez-Nunez, A. M. Echavarren. Chem. Commun. 333 (2007).
3. A. Fürtsner, P. W. Davies. Angew. Chem., Int. Ed. 46, 3410 (2007).
4. A. S. K. Hashmi. Chem. Rev. 107, 3180 (2007).
5. D. J. Gorin, B. D. Sherry, F. D. Toste. Chem. Rev. 108, 3351 (2008).
6. Z. Li, C. Brouwer, C. He. Chem. Rev. 108, 3239 (2008).
7. A. Arcadi. Chem. Rev. 108, 3266 (2008).
8. R. Skouta, C.-J. Li. Tetrahedron 64, 4917 (2008).
9. N. D. Shapiro, F. D. Toste. Synlett 5, 675 (2010).
10. J. H. Teles, S. Brode. Angew. Chem., Int. Ed. 37, 1415 (1998).
11. J. J. Kennedy-Smith, S. T. Staben, F. D. Toste. J. Am. Chem. Soc. 126, 4526 (2004).
12. S. T. Staben, J. J. Kennedy-Smith, F. D. Toste. Angew. Chem., Int. Ed. 43, 5350 (2004).
13. A. S. K. Hashmi, J. P. Weyrauch, W. Frey, J. W. Bats. Org. Lett. 6, 4391 (2004).
14. C. Nieto-Oberhuber, M. P. MuKoz, E. BuKuel, C. Nevado, D. J. Cardenas, A. M. Echavarren. Angew. Chem., Int. Ed. 43, 2402 (2004).
15. N. Mezailles, L. Ricard, F. Gagosz. Org. Lett. 7, 4133 (2005).
16. C. Nieto-Oberhuber, S. Lopez, A. M. Echavarren. J. Am. Chem. Soc. 127, 6178 (2005).
17. For a review on the synthesis of bicyclo[3.3.1]nonanes, see: (a) E. Butkus. Synlett 1827 (2001); for a review on the synthesis of the bicyclo[4.3.1]decenone skeleton of phomoidrides, see.
18. D. A. Spiegel, J. T. Njardason, I. M. McDonald, J. L. Wood. Chem. Rev. 103, 2691 (2003); for a review on the synthesis of the bicyclo[5.3.1]undecene framework of Taxol, see.
19. A. N. Boa, P. R. Jenkins, N. J. Lawrence. Contemp. Org. Synth. 1, 47 (1994).
20. S. M. Sheehan, G. Lalic, J. S. Chen, M. D. Shair. Angew. Chem., Int. Ed. 39, 2714 (2000).
21. R. M. A. Lavigne, M. Riou, M. Girardin, L. Morency, L. Barriault. Org. Lett. 7, 5921 (2005).
22. For terminal alkynes, 10 mol % W(CO)5(THF) is required, see.
23. N. Iwasawa, K. Maeyama. J. Am. Chem. Soc. 120, 1928 (1998); for substituted alkynes, a stoichiometric amount of W(CO)5(THF) is required, see.
24. 2-mediated cyclization, see.
25. K. Imamura, E. Yoshikawa, V. Gevorgyan, Y. Yamamoto. Tetrahedron Lett. 40, 4081 (1999).
26. F. Barabé, G. Bétournay, G. Bellavance, L. Barriault. Org. Lett. 10, 4236 (2009).
27. R. Ciochina, R. B. Grossman. Chem. Rev. 106, 3963 (2006).
28. For isolation of hyperforin, see: (a) A. I. Gurevich, V. N. Dobrynin, M. N. Kolosov, S. A. Popravko, I. D. Riabova. Antibiotiki 16, 510 (1971).
29. N. S. Bystrov, B. K. Chernov, V. N. Dobrynin, M. N. Kolosov. Tetrahedron Lett. 2791 (1975); for synthetic studies, see.
30. G. Mehta, M. K. Bera. Tetrahedron Lett. 50, 3519 (2009).
31. G. Mehta, M. K. Bera. Tetrahedron Lett. 49, 1417 (2008).
32. Y. Shimizu, A. Kuramochi, H. Usuda, M. Kanai, M. Shibasaki. Tetrahedron Lett. 48, 4173 (2007).
33. K. C. Nicolaou, G. E. A. V. Jeso. Angew. Chem., Int. Ed. 44, 3895 (2005); for total synthesis, see.
34. Y. Shimizu, S.-L. Shi, H. Usuda, M. Kanai, M. Shibasaki. Angew. Chem., Int. Ed. 49, 1103 (2010).
35. Y. Shimizu, S.-L. Shi, H. Usuda, M. Kanai, M. Shibasaki. Tetrahedron 66, 6569 (2010).
36. J. T. Njardarson. Tetrahedron 67, 7631 (2011).
37. J.-A. Richard, R. H. Pouwer, D. Y.-K. Chen. Angew. Chem., Int. Ed. 51, 4536 (2011).
38. B. Sow, G. Bellavance, F. Barabé, L. Barriault. Beilstein J. Org. Chem. 7, 1007 (2011).
39. J. K. Dankwardt. Tetrahedron Lett. 42, 5809 (2001).
40. M. H. Suhre, M. Reif, F. Kirsch. Org. Lett. 7, 3925 (2005).
41. S. T. Staben, J. J. Kennedy-Smith, D. Huang, B. K. Corkey, R. L. LaLonde, F. D. Toste. Angew. Chem., Int. Ed. 45, 5991 (2006).
42. X. Linghu, J. J. Kennedy-Smith, F. D. Toste. Angew. Chem., Int. Ed. 46, 7671 (2007).
43. K. Lee, P. H. Lee. Adv. Synth. Catal. 349, 2092 (2007).
44. J. T. Binder, B. Crone, T. T. Haug, H. Menz, S. F. Kirsch. Org. Lett. 10, 1025 (2008).
45. H. Ito, H. Ohmiya, M. Sawamura. Org. Lett. 12, 4380 (2010).
46. J. A. Kozak, B. O. Patrick, G. R. Dake. J. Org. Chem. 75, 8585 (2010).
47. E. C. Minnihan, S. L. Colletti, F. D. Toste, H. C. Shen. J. Org. Chem. 72, 6287 (2007).
48. C. Nevado, D. J. Cardenas, A. M. Echavarren. Chem.-Eur. J. 9, 2627 (2003).
49. P. Mauleón, R. M. Zeldin, A. Z. González, F. D. Toste. J. Am. Chem. Soc. 131, 6348 (2009).
50. D. Benitez, N. D. Shapiro, E. Tkatchouk, Y. Wang, W. A. Goddard, F. D. Toste. Nat. Chem. 1, 482 (2009).
51. M. Alcarazo, T. Stork, A. Anoop, W. Thiel, A. Fürstner. Angew. Chem., Int. Ed. 49, 2542 (2010).
52. F. Barabé, P. Levesque, I. Korobkov, L. Barriault. Org. Lett. 13, 5580 (2011).
53. D. Benitez, E. Tkatchouk, A. Z. Gonzalez, W. A. Goddard, F. D. Toste. Org. Lett. 11, 4798 (2009).