Total synthesis of Brevetoxin A

Organic Letters

Volumn 11, Issue 2, 2009, Pages 489-492

  Crimmins, Michael T ^a   Zuccarello, J Lucas ^a   Ellis, J Michael ^a   McDougall, Patrick J ^a   Haile, Pamela A ^a   Parrish, Jonathan D ^a   Emmitte, Kyle A ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; BREVETOXIN A; MARINE TOXIN; OXOCIN DERIVATIVE;

ARTICLE; CHEMISTRY; ENZYME SPECIFICITY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALDEHYDES; ALKENES; MARINE TOXINS; OXIDATION-REDUCTION; OXOCINS; SUBSTRATE SPECIFICITY;

EID: 61449264730     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802710u     Document Type: Article

References (41)

1. (a) Fuwa, H.; Sasaki, M. Curr. Opin. Drug Discovery Dev. 2007, 10, 784.
2. (b) Inoue, M. Chem. Rev. 2005, 105, 4379.
3. (c) Nakata, I. Chem. Rev. 2005, 105, 4314.
4. (d) Kadota, I.; Yamamoto, Y. Acc. Chem. Res. 2005, 38, 423.
5. (e) Sasaki, M.; Fuwa, H. Synlett 2004, 11, 1851.
6. (f) Evans, P. A.; Delouvrié, B. Curr. Opin. Drug Discovery Dev. 2002, 5, 986.
7. (g) Marmsäter, F. P.; West, F. G. Chem.-Eur. J. 2002, 8, 4346.
8. (h) Mori, Y. Chem.-Eur. J. 1997, 3, 849.
9. (c) Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953.
10. (a) Shimizu, Y.; Chou, H. N.; Bando, H.; Vanduyne, G.; Clardy, J. C. J. Am. Chem. Soc. 1986, 108, 514.
11. (b) Shimizu, Y.; Chou, H.-N.; Bando, H.; Van Duyne, G.; Clardy, J. C. J. Chem. Soc., Chem. Commun. 1986, 1656.
12. (c) 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.
13. (a) Michelliza, S.; Abraham, W. M.; Jacocks, H. M.; Schuster, T.; Baden, D. G. ChemBioChem 2007, 8, 2233.
14. (b) Naar, J. P.; Flewelling, L. J.; Lenzi, A.; Abbott, J. P.; Granholm, A.; Jacocks, H. M.; Gannon, D.; Henry, M.; Pierce, R.; Baden, D. G.; Wolny, J.; Landsberg, J. H. Toxicon 2007, 50, 707.
15. (c) Kirkpatrick, B.; Fleming, L. E.; Backer, L. C.; Bean, J. A.; Tamer, R.; Kirkpatrick, G.; Kane, T.; Wanner, A.; Dalpra, D.; Reich, A.; Baden, D. G. Harmful Algae 2006, 5, 526.
16. (d) Fleming, L. E.; Backer, L. C.; Baden, D. G. Environ. Health Persp. 2005, 113, 618, and references therein.
17. (a) Nicolaou, K. C.; Yang, Z.; Shi, G.-Q.; Gunzner, J. L.; Agrios, K. A.; Gärtner, P. Nature 1998, 392, 264.
18. (b) Nicolaou, K. C.; Bunnage, M. E.; McGarry, D. G.; Shi, S.; Somers, P. K.; Wallace, P. A.; Chu, X.-J.; Agrios, K. A.; Gunzner, J. L.; Yang, Z. Chem. - Eur. J. 1999, 5, 599.
19. (c) Nicolaou, K. C.; Wallace, P. A.; Shi, S.; Ouellette, M. A.; Bunnage, M. E.; Gunzner, J. L.; Agrios, K. A.; Shi, G.-q.; Gärtner, P.; Yang, Z. Chem. - Eur. J. 1999, 5, 618.
20. (d) Nicolaou, K. C.; Shi, G.-q.; Gunzner, J. L.; Gärtner, P.; Wallace, P. A.; Ouellette, M. A.; Shi, S.; Bunnage, M. E.; Agrios, K. A.; Veale, C. A.; Hwang, C.-K.; Hutchinson, J.; Prasad, C. V. C.; Ogilvie, W. W.; Yang, Z. Chem. - Eur. J. 1999, 5, 628.
21. (e) Nicolaou, K. C.; Gunzner, J. L.; Shi, G.-q.; Agrios, K. A.; Gärtner, P.; Yang, Z. Chem. - Eur. J. 1999, 5, 646.
22. (a) Crimmins, M. T.; McDougall, P. J.; Ellis, J. M. Org. Lett. 2006, 8, 4079.
23. (b) Crimmins, M. T.; Zuccarello, J. L.; Cleary, P. A.; Parrish, J. D. Org. Lett. 2006, 8, 15.
24. (c) Crimmins, M. T.; McDougall, P. J.; Emmitte, K. A. Org. Lett. 2005, 7, 4033.
25. (d) Crimmins, M. T.; Cleary, P. A. Heterocycles 2003, 61, 87.
26. (a) Horner, L. L.; Hoffmann, H.; Wippel, H. G.; Klahre, G. Chem.Ber. 1959, 92, 2499.
27. (b) Buss, A. D.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1985, 2307, and references therein.
28. (c) For the use of LDA in Horner-Wittig reactions, see: Earnshaw, C.; Wallis, C. J.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1979, 3099.
29. (a) Freeman, P. K.; Hutchinson, L. L. J. Org. Chem. 1980, 45, 1924.
30. (b) Ireland, R. E.; Smith, M. G. J. Am. Chem. Soc. 1988, 110, 854.
31. Attempts to prepare the phosphine oxide with the C21 hydroxyl or MOP acetal directly were hampered by purification difficulties and lower yields, respectively.
32. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
33. Corey, E. J.; Shimoji, K. Tetrahedron Lett. 1983, 24, 169.
34. (a) Griffith, W. P.; Ley, S. V.; Whitcombe, G. P.; White, A. D. J. Chem. Soc., Chem. Commun. 1987, 1625.
35. (b) Griffith, W. P.; Ley, S. V. Aldrichim. Acta 1990, 23, 13.
36. Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 287.
37. 2IPh/MeOH conditions did not cause equilibration.
38. Nicolaou, K. C.; Prasad, C. V. C.; Hwang, C.-K.; Duggan, M. E.; Veale, C. A. J. Am. Chem. Soc. 1989, 111, 5321.
39. Hansen, T. M.; Florence, G. J.; Lugo-Mas, P.; Chen, J. H.; Abrams, J. N.; Forsyth, C. J. Tetrahedron Lett. 2003, 44, 57.
40. Schreiber, J.; Maag, H.; Hashimoto, N.; Eschenmoser, A. Angew. Chem., Int. Ed. Engl. 1971, 10, 330.
41. See the Supporting Information.