A Pauson-Khand and ring-expansion approach to the aquariane ring system

Organic Letters

Volumn 8, Issue 15, 2006, Pages 3195-3198

  Thornton, Paul D ^a   Burnell, D Jean ^a  

^a DALHOUSIE UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE;

ANIMAL; ANTHOZOA; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANIMALS; ANTHOZOA; DITERPENES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33746908510     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0609715     Document Type: Article

References (21)

1. Taglialatela-Scafati, O.; Deo-Jangra, U.; Campbell, M.; Roberge, M.; Andersen, R. J. Org. Lett. 2002, 4, 4085-4088.
2. Taglialatela-Scafati, O.; Craig, K. S.; Rebérioux, D.; Roberge, M.; Andersen, R. J. Eur. J. Org. Chem. 2003, 3515-3523.
3. (a) Look, S. A.; Fenical, W.; Van Engen, D.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 5026-5027.
4. (b) Pordesimo, E. O.; Schmitz, F. J.; Ciereszko, L. S.; Hossain, M. B.; van der Helm, D. J. Org. Chem. 1991, 56, 2344-2357.
5. (c) Banjoo, D.; Mootoo, B. S.; Ramsewak, R. S.; Sharma, R.; Lough, A. J.; McLean, S.; Reynolds, W. F. J. Nat. Prod. 2002, 65, 314-318.
6. For recent reviews, see: (a) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263-3283.
7. (b) Blanco-Urgoiti, J.; Anorbe, L.; Perez-Serrano, L.; Dominguez, G.; Perez-Castells, J. Chem. Soc. Rev. 2004, 33, 32-42.
8. Yamaguchi, M.; Shibato, K.; Fujiwara, S.; Hirao, I. Synthesis 1986, 421-422.
9. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485-1491.
10. Fujita, M.; Hiyama, T. J. Org. Chem. 1988, 53, 5415-5421.
11. (a) Takeda, N.; Imamoto, T. J. Am. Chem. Soc. 1989, 111, 4392-4398.
12. (b) Takeda, N.; Imamoto, T. Org. Synth. 1998, 76, 228-238.
13. Jeong, N.; Chung, Y. K.; Lee, B. Y.; Lee, S. H.; Yoo, S. Synlett 1991, 204-206.
14. (a) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289-5292.
15. (b) Sugihara, T.; Yamada, M.; Yamaguchi, M.; Nishizawa, M. Synlett 1999, 771-773.
16. Proposed mechanism of the Pauson-Khand process: Magnus, P.; Principe, L. M. Tetrahedron Lett. 1985, 26, 4851-4854.
17. Evans, D. A.; Golob, A. M. J. Am. Chem. Soc. 1975, 97, 4765-4766.
18. Paquette, L. A. Tetrahedron 1997, 41, 13971-14020.
19. Paquette, L. A.; Teleha, C. A.; Taylor, R. T.; Maynard, G. D.; Rogers, R. D.; Gallucci, J. C.; Springer, J. P. J. Am. Chem. Soc. 1990, 112, 265-277.
20. Luche, J. L. J. Am. Chem. Soc. 1978, 100, 2226-2227.
21. Another example of a Grob fragmentation to produce a nine-membered ring: Yang, J.; Long, Y. O.; Paquette, L. A. J. Am. Chem. Soc. 2003, 125, 1567-1574.