Synthesis of the tetracyclic core of berkelic acid using gold(I)-catalyzed hydroarylation and oxidative radical cyclizations

Organic Letters

Volumn 14, Issue 23, 2012, Pages 5820-5823

  Brimble, Margaret A ^a   Haym, Isabell ^a   Sperry, Jonathan ^a   Furkert, Daniel P ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

BERKELIC ACID; GOLD; SPIRO COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

CATALYSIS; CYCLIZATION; GOLD; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84870865334     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302536j     Document Type: Article

References (43)

1. Wilson, Z. E.; Brimble, M. A. Nat. Prod. Rep. 2009, 26, 44-71
2. Stierle, A. A.; Stierle, D. B. J. Org. Chem. 2006, 71, 5357-5360
3. Buchgraber, P.; Snaddon, T. N.; Wirtz, C.; Mynott, R.; Goddard, R.; Fürstner, A. Angew. Chem., Int. Ed. 2008, 47, 8450-8454
4. Wu, X.; Zhou, J.; Snider, B. B. Angew. Chem., Int. Ed. 2009, 48, 1283-1286
5. Bender, C. F.; Yoshimoto, F. K.; Paradise, C. L.; De Brabander, J. K. J. Am. Chem. Soc. 2009, 131, 13350-13352
6. Wenderski, T. A.; Marsini, M. A.; Pettus, T. R. R. Org. Lett. 2011, 13, 118-121
7. Fañanás, F. J.; Mendoza, A.; Arto, T.; Temelli, B.; Rodríguez, F. Angew. Chem., Int. Ed. 2012, 51, 4930-4933
8. McLeod, M. C.; Wilson, Z. E.; Brimble, M. A. Org. Lett. 2011, 13, 5382-5385
9. McLeod, M. C.; Wilson, Z. E.; Brimble, M. A. J. Org. Chem. 2012, 77, 400-416
10. Hashmi, A. S. K.; Lothschütz, C.; Döpp, R.; Ackermann, M.; Becker, J.; Rudolph, M.; Scholz, C.; Rominger, F. Adv. Syn. Catal. 2012, 354, 133-147
11. Lindberg, M.; Hellberg, S.; Björk, S.; Gotthammar, B.; Högberg, T.; Persson, K.; Schwarcz, R.; Luthman, J.; Johansson, R. Eur. J. Med. Chem. 1999, 34, 729-744
12. Brown, P. E.; Lewis, R. A. J. Chem. Soc., Perkin Trans. 1 1992, 573-577
13. Harfenist, M.; Thom, E. J. Org. Chem. 1972, 37, 841-848
14. Jia, C.; Lu, W.; Oyamada, J.; Kitamura, T.; Matsuda, K.; Irie, M.; Fujiwara, Y. J. Am. Chem. Soc. 2000, 122, 7252-7263
15. Jia, C.; Piao, D.; Kitamura, T.; Fujiwara, Y. J. Org. Chem. 2000, 65, 7516-7522
16. Pastine, S. J.; Youn, S. W.; Sames, D. Org. Lett. 2003, 5, 1055-1058
17. Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918
18. Nishizawa, M.; Takao, H.; Yadav, V. K.; Imagava, H.; Sugihara, T. Org. Lett. 2003, 5, 4563-4565
19. Menon, R. S.; Findley, A. D.; Bissember, A. C.; Banwell, M. G. J. Org. Chem. 2009, 74, 8901-8903
20. Boormann, T. C.; Larrosa, I. Chem. Soc. Rev. 2011, 40, 1910-1925
21. McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885-1898
22. Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976-1991
23. Lewis, J. C.; Coehl, P. S.; Arnold, F. H. Chem. Soc. Rev. 2011, 40, 2003-2021
24. Wang, Y.; Ji, K.; Lan, S.; Zhang, L. Angew. Chem., Int. Ed. 2012, 51, 1915-1918
25. Lykakis, I. N.; Efe, C.; Gryparis, C.; Stratakis, M. Eur. J. Org. Chem. 2011, 2334-2338
26. Rudolph, M.; Hashmi, A. S. K. Chem. Soc. Rev. 2012, 41, 2448-2462
27. Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208-3221
28. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180-3213
29. Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239-3265
30. Herrero-Goméz, E.; Nieto-Oberhuber, C.; Lopéz, S.; Benet-Buchholz, J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2006, 45, 5455-5459
31. de Armas, P.; Concepción, J. I.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez, E. J. Chem. Soc., Perkin Trans. 1 1989, 405-411
32. Francisco, C. G.; Freire, R.; Herrera, A. J.; Peréz-Martin, I.; Suárez, E. Org. Lett. 2002, 4, 1959-1961
33. Furkert, D. P.; Brimble, M. A. Org. Biomol. Chem. 2004, 2, 3573-3583
34. Meilert, K.; Brimble, M. A. Org. Biomol. Chem. 2006, 4, 2184-2192
35. Sperry, J.; Liu, Y.-C.; Brimble, M. A. Org. Biomol. Chem. 2010, 8, 29-38
36. Heusler, K.; Kalvoda, J. Angew. Chem. 1964, 76, 518-531
37. Angew. Chem., Int. Ed. 1964, 3, 525-538.
38. Goddard, C. M.; Nowick, J. S. J. Org. Chem. 2010, 75, 1822-1830
39. Walborsky, H. M.; Goedken, V. L.; Gawronsky, J. K. J. Org. Chem. 1992, 57, 410-413
40. Boudet, N.; Lachs, J. R.; Knochel, P. Org. Lett. 2007, 9, 5525-5528
41. Grimm, J. B.; Wilson, K. J.; Witter, D. J. Tetrahedron Lett. 2007, 48, 4509-4513
42. Berger, P.; Bessmernykh, A.; Caille, J.-C.; Mignonac, S. Synthesis 2006, 18, 3106-3130
43. Zhou, J.; Snider, B. B. Org. Lett. 2007, 9, 2071-2074