Pure Appl. Chem., 2013, Vol. 85, No. 6, pp. 1161-1173
http://dx.doi.org/10.1351/PAC-CON-13-01-02
Published online 2013-05-10
Gold(I)-catalyzed formation of bridged and fused carbocycles
References
- 1. F. D. , D. J. Gorin. Nature 446, 395 (2007).
- 2. For recent reviews, see.
- 2a. E. , A. M. Echavarren. Chem. Commun. 333 (2007). (http://dx.doi.org/10.1039/b612008c)
- 2b. A. , P. W. Davies. Angew. Chem., Int. Ed. 46, 3410 (2007).
- 2c. A. S. K. . Chem. Rev. 107, 3180 (2007). (http://dx.doi.org/10.1021/cr000436x)
- 2d. D. J. , B. D. Sherry, F. D. Toste. Chem. Rev. 108, 3351 (2008). (http://dx.doi.org/10.1021/cr068430g)
- 2e. Z. , C. Brouwer, C. He. Chem. Rev. 108, 3239 (2008). (http://dx.doi.org/10.1021/cr068434l)
- 2f. A. . Chem. Rev. 108, 3266 (2008). (http://dx.doi.org/10.1021/cr068435d)
- 2g. R. , C.-J. Li. Tetrahedron 64, 4917 (2008). (http://dx.doi.org/10.1016/j.tet.2008.03.083)
- 2h. N. D. , F. D. Toste. Synlett 5, 675 (2010).
- 3. J. H. , S. Brode. Angew. Chem., Int. Ed. 37, 1415 (1998). (http://dx.doi.org/10.1002/(SICI)1521-3773(19980605)37:10<1415::AID-ANIE1415>3.0.CO;2-N)
- 4a. J. J. , S. T. Staben, F. D. Toste. J. Am. Chem. Soc. 126, 4526 (2004). (http://dx.doi.org/10.1021/ja049487s)
- 4b. S. T. , J. J. Kennedy-Smith, F. D. Toste. Angew. Chem., Int. Ed. 43, 5350 (2004). (http://dx.doi.org/10.1002/anie.200460844)
- 5. A. S. K. , J. P. Weyrauch, W. Frey, J. W. Bats. Org. Lett. 6, 4391 (2004). (http://dx.doi.org/10.1021/ol0480067)
- 6. C. , M. P. MuKoz, E. BuKuel, C. Nevado, D. J. Cardenas, A. M. Echavarren. Angew. Chem., Int. Ed. 43, 2402 (2004). (http://dx.doi.org/10.1002/anie.200353207)
- 7a. N. , L. Ricard, F. Gagosz. Org. Lett. 7, 4133 (2005). (http://dx.doi.org/10.1021/ol0515917)
- 7b. C. , S. Lopez, A. M. Echavarren. J. Am. Chem. Soc. 127, 6178 (2005). (http://dx.doi.org/10.1021/ja042257t)
- 8. For a review on the synthesis of bicyclo[3.3.1]nonanes, see.
- 8a. E. . Synlett 1827 (2001); (http://dx.doi.org/10.1055/s-2001-18734)
- 8b. for a review on the synthesis of the bicyclo[4.3.1]decenone skeleton of phomoidrides, see: D. A. , J. T. Njardason, I. M. McDonald, J. L. Wood. Chem. Rev. 103, 2691 (2003); (http://dx.doi.org/10.1021/cr020408+)
- 8c. for a review on the synthesis of the bicyclo[5.3.1]undecene framework of Taxol, see: A. N. , P. R. Jenkins, N. J. Lawrence. Contemp. Org. Synth. 1, 47 (1994). (http://dx.doi.org/10.1039/co9940100047)
- 8d. S. M. , G. Lalic, J. S. Chen, M. D. Shair. Angew. Chem., Int. Ed. 39, 2714 (2000). (http://dx.doi.org/10.1002/1521-3773(20000804)39:15<2714::AID-ANIE2714>3.0.CO;2-1)
- 8e. R. M. A. , M. Riou, M. Girardin, L. Morency, L. Barriault. Org. Lett. 7, 5921 (2005). (http://dx.doi.org/10.1021/ol0527072)
- 9. For terminal alkynes, 10 mol % W(CO)5(THF) is required, see:
- 9a. N. , K. Maeyama. J. Am. Chem. Soc. 120, 1928 (1998); (http://dx.doi.org/10.1021/ja9734004)
- 9b. for substituted alkynes, a stoichiometric amount of W(CO)5(THF) is required, see: N. , N. T. Miura. J. Am. Chem. Soc. 124, 518 (2002);
- 9c. for EtAlCl2-mediated cyclization, see: K. , E. Yoshikawa, V. Gevorgyan, Y. Yamamoto. Tetrahedron Lett. 40, 4081 (1999). (http://dx.doi.org/10.1016/S0040-4039(99)00654-1)
- 10. F. , G. Bétournay, G. Bellavance, L. Barriault. Org. Lett. 10, 4236 (2009). (http://dx.doi.org/10.1021/ol901722q)
- 11. R. , R. B. Grossman. Chem. Rev. 106, 3963 (2006). (http://dx.doi.org/10.1021/cr0500582)
- 12. For isolation of hyperforin, see.
- 12a. A. I. , V. N. Dobrynin, M. N. Kolosov, S. A. Popravko, I. D. Riabova. Antibiotiki 16, 510 (1971).
- 12b. N. S. , B. K. Chernov, V. N. Dobrynin, M. N. Kolosov. Tetrahedron Lett. 2791 (1975); (http://dx.doi.org/10.1016/S0040-4039(00)75241-5)
- 12c. for synthetic studies, see: G. , M. K. Bera. Tetrahedron Lett. 50, 3519 (2009). (http://dx.doi.org/10.1016/j.tetlet.2009.03.041)
- 12d. G. , M. K. Bera. Tetrahedron Lett. 49, 1417 (2008). (http://dx.doi.org/10.1016/j.tetlet.2007.12.065)
- 12e. Y. , A. Kuramochi, H. Usuda, M. Kanai, M. Shibasaki. Tetrahedron Lett. 48, 4173 (2007). (http://dx.doi.org/10.1016/j.tetlet.2007.04.080)
- 12f. K. C. , G. E. A. V. Jeso. Angew. Chem., Int. Ed. 44, 3895 (2005); (http://dx.doi.org/10.1002/anie.200500776)
- 12g. for total synthesis, see: Y. , S.-L. Shi, H. Usuda, M. Kanai, M. Shibasaki. Angew. Chem., Int. Ed. 49, 1103 (2010). (http://dx.doi.org/10.1002/anie.200906678)
- 12h. Y. , S.-L. Shi, H. Usuda, M. Kanai, M. Shibasaki. Tetrahedron 66, 6569 (2010). (http://dx.doi.org/10.1016/j.tet.2010.05.086)
- 13a. J. T. . Tetrahedron 67, 7631 (2011). (http://dx.doi.org/10.1016/j.tet.2011.06.079)
- 13b. J.-A. , R. H. Pouwer, D. Y.-K. Chen. Angew. Chem., Int. Ed. 51, 4536 (2011). (http://dx.doi.org/10.1002/anie.201103873)
- 14. B. , G. Bellavance, F. Barabé, L. Barriault. Beilstein J. Org. Chem. 7, 1007 (2011). (http://dx.doi.org/10.3762/bjoc.7.114)
- 15a. J. K. . Tetrahedron Lett. 42, 5809 (2001). (http://dx.doi.org/10.1016/S0040-4039(01)01146-7)
- 15b. M. H. , M. Reif, F. Kirsch. Org. Lett. 7, 3925 (2005). (http://dx.doi.org/10.1021/ol0514101)
- 15c. S. T. , J. J. Kennedy-Smith, D. Huang, B. K. Corkey, R. L. LaLonde, F. D. Toste. Angew. Chem., Int. Ed. 45, 5991 (2006). (http://dx.doi.org/10.1002/anie.200602035)
- 15d. X. , J. J. Kennedy-Smith, F. D. Toste. Angew. Chem., Int. Ed. 46, 7671 (2007). (http://dx.doi.org/10.1002/anie.200702695)
- 15e. K. , P. H. Lee. Adv. Synth. Catal. 349, 2092 (2007). (http://dx.doi.org/10.1002/adsc.200700304)
- 15f. J. T. , B. Crone, T. T. Haug, H. Menz, S. F. Kirsch. Org. Lett. 10, 1025 (2008). (http://dx.doi.org/10.1021/ol800092p)
- 15g. H. , H. Ohmiya, M. Sawamura. Org. Lett. 12, 4380 (2010). (http://dx.doi.org/10.1021/ol101860j)
- 16a. J. A. , B. O. Patrick, G. R. Dake. J. Org. Chem. 75, 8585 (2010). (http://dx.doi.org/10.1021/jo102036n)
- 16b. E. C. , S. L. Colletti, F. D. Toste, H. C. Shen. J. Org. Chem. 72, 6287 (2007). (http://dx.doi.org/10.1021/jo071014r)
- 16c. C. , D. J. Cardenas, A. M. Echavarren. Chem.—Eur. J. 9, 2627 (2003). (http://dx.doi.org/10.1002/chem.200204646)
- 17a. P. , R. M. Zeldin, A. Z. González, F. D. Toste. J. Am. Chem. Soc. 131, 6348 (2009). (http://dx.doi.org/10.1021/ja901649s)
- 17b. D. , N. D. Shapiro, E. Tkatchouk, Y. Wang, W. A. Goddard, F. D. Toste. Nat. Chem. 1, 482 (2009). (http://dx.doi.org/10.1038/nchem.331)
- 17c. M. , T. Stork, A. Anoop, W. Thiel, A. Fürstner. Angew. Chem., Int. Ed. 49, 2542 (2010). (http://dx.doi.org/10.1002/anie.200907194)
- 18. F. , P. Levesque, I. Korobkov, L. Barriault. Org. Lett. 13, 5580 (2011). (http://dx.doi.org/10.1021/ol202314q)
- 19. D. , E. Tkatchouk, A. Z. Gonzalez, W. A. Goddard, F. D. Toste. Org. Lett. 11, 4798 (2009). (http://dx.doi.org/10.1021/ol9018002)
