Improved synthesis of the ABCDE fragment of brevetoxin A

Organic Letters

Volumn 8, Issue 18, 2006, Pages 4079-4082

  Crimmins, Michael T ^a   McDougall, Patrick J ^a   Ellis, J Michael ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BREVETOXIN A; MARINE TOXIN; OXOCIN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; SYNTHESIS;

MARINE TOXINS; MOLECULAR STRUCTURE; OXOCINS;

EID: 33748935937     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0615782     Document Type: Article

References (28)

1. Isolation: (a) Shimizu, Y.; Chou, H.-N.; Bando, H. J. Am. Chem. Soc. 1986, 108, 514.
2. (b) Pawlak, J.; Tempesta, M. S.; Golik, J.; Zagorski, M. G.; Lee, M. S.; Nakanishi, K.; Iwashita, T.; Gross, M. L.; Tomer, K. B. J. Am. Chem. Soc. 1987, 109, 1144.
3. Previous synthesis: Nicolaou, K. C.; Yang, Z.; Shi, G.-q.; Gunzner, J. L.; Agrios, K. A.; Gärtner, P. Nature 1998, 392, 264.
4. Nicolaou, K. C. Gunzner, J. L.; Shi, G.-q.; Agrios, K. A.; Gärtner, P.; Yang, Z. Chem.-Eur. J. 1999, 5, 646 and references therein.
5. Crimmins, M. T.; McDougall, P. J.; Emmitte, K. A. Org. Lett. 2005, 7, 4033.
6. Crimmins, M. T.; Zuccarello, J. L.; Cleary, P. A. Org. Lett. 2006, 8, 159.
7. For a recent review on convergent strategies for synthesis of polycyclic ethers, see: Inoue, M. Chem. Rev. 2005, 105, 4379.
8. Crimmins, M. T.; McDougall, P. J. Org. Lett. 2003, 5, 591.
9. Crimmins, M. T.; Emmitte, K. A.; Katz, J. D. Org. Lett. 2000, 2, 2165.
10. Mancuso, A. J.; Huang, S.; Swern, D. J. Org. Chem. 1978, 43, 2480.
11. Oishi, T.; Nakata, T. Acc. Chem. Res. 1984, 17, 338.
12. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
13. Gemal, A. L.; Luche, J. L. J. Am. Chem. Soc. 1981, 103, 5454.
14. Crabtree, R. H.; Felkin, H.; Fillebeen-Khan, T.; Morris, G. E. J. Organomet. Chem. 1979, 168, 183.
15. Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. Tetrahedron 1986, 42, 3021.
16. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
17. (a) Crimmins, M. T.; Stanton, M. G.; Allwein, S. P. J. Am. Chem. Soc. 2002, 124, 5958.
18. (b) Keck, G. E.; Abbott, D. E. Tetrahedron Lett. 1984, 25, 1883.
19. Miller, S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108.
20. (a) Alvarez-Ibarra, C.; Arias, S.; Bañon, G.; Fernandez, M. J.; Rodriguez, M.; Sinisterra, V. J. Chem. Soc. Chem. Commun. 1987, 1509.
21. (b) Paterson, I.; Yeung, K.-S.; Smaill, J. B. Synlett 1993, 774.
22. Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291.
23. Ojima, I.; Kogure, T. Organometalics 1982, 1, 1390.
24. Johnson, H. W. B.; Majumder, U.; Rainier, J. D. J. Am. Chem. Soc. 2005, 127, 848.
25. Gilbert, M.; Ferrer, M.; Sanchez-Baeza, F.; Messeguer, A. Tetrahedron 1997, 53, 8643.
26. Inoue, M.; Yamashita, S.; Tatami, A.; Miyazaki, K.; Hirama, M. J. Org. Chem. 2004, 69, 2797.
27. Paquette, L. A.; Sturino, C. F.; Wang, X.; Prodger, J. C.; Koh, D. J. Am. Chem. Soc. 1996, 118, 5620.
28. Griffith, W. P.; Ley, S. V.; Whitcombe, G. P.; White, A. D. J. Chem. Soc. Chem. Commun. 1987, 1625.