Synthesis of an A-E gambieric acid subunit with use of a C-glycoside centered strategy

Organic Letters

Volumn 9, Issue 11, 2007, Pages 2227-2230

  Roberts, Scott W ^a   Rainier, Jon D ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CIGUATOXIN; ETHER DERIVATIVE; GAMBIERIC ACID A; UNCLASSIFIED DRUG;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DINOFLAGELLATE; METABOLISM;

ANIMALS; CIGUATOXINS; DINOFLAGELLIDA; ETHERS, CYCLIC; MOLECULAR STRUCTURE;

EID: 34250631332     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0707970     Document Type: Article

References (48)

1. (a) Nagai, H.; Torigoe, K.; Satake, M.; Murata, M.; Yasumoto, T.; Hirota, H. J. Am. Chem. Soc., 1992, 114, 1102.
2. (b) Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem., 1992, 57, 5448.
3. Morohashi, A.; Satake, M.; Nagai, H.; Oshima, Y.; Yasumoto, T. Tetrahedron, 2000, 56, 8995.
4. 50 for ciguatoxin (CTX) in mice is 0.35 μg/kg. See refs 4 and 6.
5. Inoue, M.; Hirama, M.; Satake, M.; Sugiyama, K.; Yasumoto, T. Toxican, 2003, 41, 469.
6. Brevenal and gambierol are two other members of this family that inhibit PbTx-3 binding. See: LePage, K. T.; Rainier, J. D.; Johnson, H. W. B.; Baden, D. G.; Murray, T. F. Submitted for publication.
7. Sakamoto, B.; Nagai, H.; Hokama, Y. Phycologia, 1996, 35, 350.
8. Nagai, H.; Makami, Y.; Yazawa, K.; Gonoi, T.; Yasumoto, T. J. Antibiot., 1993, 46, 520.
9. A, 5000 L fermentation broth yielded 14.9 mg of GA's A-D.
10. (a) Evans, P. A.; Roseman, J. D.; Garber, L. T. J. Org. Chem., 1996, 61, 4880.
11. (b) Kadota, I.; Oguro, N.; Yamamoto, Y. Tetrahedron Lett., 2001, 42, 3645.
12. (c) Kadota, I.; Takamura, H.; Yamamoto, Y. Tetrahedron Lett., 2001, 42, 3649.
13. (d) Clark, J. S.; Fessard, T. C.; Wilson, C. Org. Lett., 2004, 6, 1773.
14. (e) Sato, K.; Sasaki, M. Org. Lett., 2005, 7, 2441.
15. (f) Clark, J. S.; Kimber, M. C.; Robertson, J.; McErlean, C. S. P.; Wilson, C. Angew. Chem., Int. Ed., 2005, 44, 6157.
16. (g) Sato, K.; Sasaki, M. Angew. Chem., Int. Ed., 2007, 46, 2518.
17. For an example of the use of this approach in the generation of ladder toxins see: (a) Majumder, U.; Cox, J. M.; Johnson, H. W. B.; Rainier, J. D. Chem. Eur. J., 2006, 12, 1736.
18. (b) Johnson, H. W. B.; Majumder, U.; Rainier, J. D. Chem. Eur. J., 2006, 12, 1747.
19. We employed a similar sequence in our formal total synthesis of hemibrevetoxin B. See: (a) Rainier, J. D.; Allwein, S. P.; Cox, J. M. Org. Lett., 2000, 2, 231.
20. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem., 2001, 66, 1380.
21. Available in 11 steps from L-glucose. See the Supporting Information and: (a) Boulineau, F. P.; Wei, A. J. Org. Chem., 2004, 69, 3391.
22. (b) Boulineau, F. P.; Wei, A. Org. Lett., 2004, 6, 119.
23. Roberts, S. W.; Rainier, J. D. Org. Lett., 2005, 7, 1141.
24. Majumder, U.; Cox, J. M.: Rainier, J. D. Org. Lett., 2003, 5, 913.
25. Paquette, L. A.; Oplinger, J. A. J. Org. Chem., 1988, 53, 2953.
26. Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem., 1994, 59, 2668.
27. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett., 1999, 1, 953.
28. Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc., 2001, 123, 6543.
29. (a) Allwein, S. P.; Cox, J. M.; Howard, B. E.; Johnson, H. W. B.; Rainier, J. D. Tetrahedron, 2002, 58, 1997.
30. (b) Rainier, J. D.; Allwein, S. P. Tetrahedron Lett., 1998, 39, 9601.
31. For a theoretical discussion of the effect of substitution on anhydride formation see: Orendt, A. M.; Roberts, S. W.; Rainier, J. D. J. Org. Chem., 2006, 71, 5565.
32. We observed a similar result in our hemibrevetoxin B work. See ref 11.
33. (a) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc., 1997, 119, 6496.
34. (b) White, J. D.; Xu, Q.; Lee, C.-S.; Valeriote, F. A. Org. Biomol. Chem., 2004, 2, 2092.
35. We also examined the coupling of 24 with enol silanes without any success.
36. Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Smith, D. M.; Woerpel, K. A. J. Am. Chem. Soc., 2005, 127, 10879.
37. (a) Evans, D. A.; Allison, B. D.; Yang, M. G.; Masse, C. E. J. Am. Chem. Soc., 2001, 123, 10840.
38. (b) Evans, D. A.; Allison, B. D.; Yang, M. G. Tetrahedron Lett., 1999, 40, 4457.
39. See ref 10 and: Johnson, H. W. B.; Majumder, U.; Rainier, J. D. J. Am. Chem. Soc., 2005, 127, 848.
40. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn., 1979, 52, 1989.
41. Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. B. J. Am. Chem. Soc., 1990, 112, 3875.
42. As 30 decomposed upon standing at -40 °C for 12 h in neutralized chloroform, we believe that the moderate yield for this transformation is a result of the relative instability of 30. We plan to address this problem when we turn to the real GA precursor.
43. Related reactions have been reported. See refs 10, 26, 31 and: (a) Stille, J. R.; Grubbs, R. H. J. Am. Chem. Soc., 1986, 108, 855.
44. (b) Stille, J. R.; Santarsiero, B. D.; Grubbs, R. H. J. Org. Chem., 1990, 55, 843.
45. (c) Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc., 1996, 118, 1565.
46. (d) Nicolaou, K. C.; Postema, M. H. D.; Yue, E. W.; Nadin, A. J. Am. Chem. Soc., 1996, 118, 10335.
47. (a) Allwein, S. P.; Cox, J. M.; Howard, B. E.; Johnson, H. W. B.; Rainier, J. D. Tetrahedron, 2002, 58, 1997.
48. (b) Majumder, U.; Rainier, J. D. Tetrahedron Lett., 2005, 46, 7209.