Total synthesis of the terpenoid buddledone A: 11-membered ring-closing metathesis

Organic Letters

Volumn 14, Issue 7, 2012, Pages 1661-1663

  Cai, Zhengxin ^a   Yongpruksa, Nattawut ^a   Harmata, Michael ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANONE; BUDDLEDONE A; METHYLETHYL KETONE; SESQUITERPENE;

ARTICLE; BUDDLEJA; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

BUDDLEJA; BUTANONES; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; SESQUITERPENES;

EID: 84859608335     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300400x     Document Type: Article

References (38)

1. Liao, Y. H.; Houghton, P. J.; Hoult, J. R. S. J. Nat. Prod. 1999, 62, 1241-1245
2. Li, Y.-Y.; Lu, J.-H.; Li, Q.; Zhao, Y.-Y.; Pu, X.-P. Eur. J. Pharmacol. 2008, 579, 134-140
3. Lee, Y. J.; Kang, D. G.; Kim, J. S.; Lee, H. S. Exp. Biol. Med. (London, U. K.) 2008, 233, 694-700
4. Zerumbone is a major component of the essential oil of wild ginger, Zingiber zerumbet: Dev, S. Tetrahedron. 1960, 8, 171-180
5. Kalsi, P. S.; Singh, O. S.; Chhabra, B. R. Phytochemistry. 1978, 17, 576
6. Mathes, H. W. P.; Luu, B.; Ourisson, G. Phytochemistry 1980, 19, 2643
7. Ozaki, Y; Kawahara, N.; Harada, M. Chem. Pharm. Bull. 1991, 39, 2353-2356
8. Kim, M.; Miyamoto, S.; Yasui, Y.; Oyama, T.; Murakami, A.; Tanaka, T. Int. J. Cancer. 2009, 124, 264-271
9. Huang, G. C; Chien, T. Y.; Chen, L. G.; Wang, C. C. Planta Med. 2005, 71, 219-224
10. Sung, B.; Jhurani, S.; Ahn, K. S.; Mastuo, Y.; Yi, T.; Guha, S.; Liu, M.; Aggarwal, B. B. Cancer Res. 2008, 68, 8938-8944
11. Dai, J. R.; Cardellina, J. H., II.; McMahon, J. B.; Boyd, M. R. Nat. Prod. Lett. 1997, 10, 115-118
12. Hosoya, T.; Arai, M. A.; Koyano, T.; Kowithayakorn, T.; Ishibashi, M. ChemBioChem 2008, 9, 1082-1092
13. Winkler, J. D.; Holland, J. M.; Kasparec, J.; Axelsen, P. H. Tetrahedron 1999, 55, 8199-8214
14. Fürstner, A.; Radkowski, K.; Wirtz, C.; Goddard, R.; Lehmann, C. W.; Mynott, R. J. Am. Chem. Soc. 2002, 124, 7061-7069
15. Wipf, P.; Stephenson, C. R. J.; Walczak, M. A. A. Org. Lett. 2004, 6, 3009-3012
16. Nicolaou, K. C.; Montagnon, T.; Vassilikogiannakis, G.; Mathison, C. J. N. J. Am. Chem. Soc. 2005, 127, 8872-8888
17. Fürstner, A.; Müller, C. Chem. Commun. 2005, 5583-5585
18. Matsumura, T.; Akiba, M.; Arai, S.; Nakawa, M.; Nishida, A. Tetrahedron Lett. 2007, 48, 1265-1268
19. Lejkowski, M.; Gais, H.-J.; Banerjee, P.; Vermeeren, C. J. Am. Chem. Soc. 2006, 128, 15378-15379
20. Tanabe, K.; Fujie, A.; Ohmori, N.; Hiraga, Y.; Kouima, S.; Ohkata, K. Bull. Chem. Soc. Jpn. 2007, 80, 1597-1604
21. Cluzeau, J.; Oishi, S.; Ohno, H.; Wang, Z.; Evans, B.; Peiper, S. C.; Fujii, N. Org. Biomol. Chem. 2007, 5, 1915-1923
22. Brown, M. K.; Hoveyda, A. H. J. Am. Chem. Soc. 2008, 130, 12904-12906
23. Kaewpet, M.; Odell, B.; King, M. A.; Banerji, B.; Scholfield, C. J.; Claridge, T. D. W. Org. Biomol. Chem. 2008, 6, 3476-3485
24. Braddock, D. C.; Millan, D. S.; Pérez-Fuertess, Y.; Pouwer, R. H.; Sheppard, R. N.; Solanki, S.; White, A. J. P. J. Org. Chem. 2009, 74, 1835-1841
25. Pospísil, J.; Müller, C.; Fürstner, A. Chem.-Eur. J. 2009, 15, 5956-5968
26. Majumda, K.; Chattopadhyay, B.; Ansary, I. Can. J. Chem. 2009, 87, 472-477
27. Prunet, J. Eur. J. Org. Chem. 2011, 3634-3647
28. El Sukkari, H.; Gesson, J.-P.; Renoux, B. Tetrahedron Lett. 1998, 39, 4043-4046
29. Vassilikogiannakis, G.; Margaros, I.; Tofi, M. Org. Lett. 2004, 6, 205-208
30. Hoye, T. R.; Promo, M. A. Tetrahedron Lett. 1999, 40, 1429-1432
31. Arisawa, M.; Kato, C.; Kaneko, H.; Nishida, A.; Nakagawa, M. J. Chem. Soc., Perkin Trans. 1 2000, 1873-1876
32. Ronsheim, M. D.; Zercher, C. K. J. Org. Chem. 2003, 68, 1878-1885
33. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179
34. Yamamoto, H.; Saito, S. Pure Appl. Chem. 1999, 71, 239-245
35. Pentzer, E. B.; Gadzikwa, T.; Nguyen, S. T. Org. Lett. 2008, 10, 5613-5615
36. Jung, M. E.; Piizzi, G. Chem. Rev. 2005, 105, 1735-1766
37. Kotha, S.; Dipak, M. K. Tetrahedron 2012, 68, 397-421
38. Hong, S. H.; Sanders, D. P.; Lee, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2005, 127, 17160-17161