Formal synthesis of fumonisin B 1, a potent sphingolipid biosynthesis inhibitor

Tetrahedron Letters

Volumn 53, Issue 26, 2012, Pages 3233-3236

  Chandrasekhar, Srivari ^a   Sreelakshmi, Lella ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

d Mannitol; Fumonisin B 1; MacMillan hydroxylation; Ring closing metathesis; Sphingolipid

Indexed keywords

FUMONISIN B1;

ARTICLE; ASYMMETRIC SYNTHESIS; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROXYLATION; MACMILLAN ALPHA HYDROXYLATION; REDUCTION; RING CLOSING METATHESIS; SHARPLESS EPOXIDATION; STEREOCHEMISTRY;

EID: 84861526221     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.04.030     Document Type: Article

References (38)

1. W.F.O. Marasas, P.E. Nelson, and T.A. Toussoun Toxigenic Fusarium Species: Identity and Mycotoxicology, 216 1984 The Pennsylvania State University Press University Park, PA
2. E.W. Sydenham, P.G. Thiel, W.F.O. Marasas, G.S. Shephard, D.J. Van Schalkwyk, and K.R. Koch J. Agric. Food. Chem. 38 1900 1990
3. F.C. Chu, and G.Y. Li Appl. Environ. Microbiol. 60 1994 847
4. W.F.O. Marasas C.J. Pfeiffer, Cancer of the Oesophagus, 1 1982 GRC Press Boca Raton, FL 29
5. C.S. Yang Cancer Res. 40 1980 2633
6. P.G. Thiel, G.S. Shephard, E.W. Sydenham, W.F.O. Marasas, P.E. Nelson, and T.M. Wilson J. Agric. Food. Chem. 39 1991 109
7. L.R. Harrison, B.M. Colvin, J.T. Green, L.E. Newman, and J.R. Cole J. Vet. Diagn. InVest. 2 1990 217
8. J.P. Rhedder, W.F.O. Marasas, P.G. Thiel, E.W. Sydenham, G.S. Shephard, D.E. Van Schalkwyk, and P. Wang Teratology J. Phytopathology 82 1992 353
9. Sadler, T. W.; Merrill, A. H.; Stevens, V. L.; Sullards, M. C.; Wang, Teratology 2002, 66, 169
10. K. Hendricks Epidemiology 10 1999 198
11. B.A. Blackwell, O.E. Edwards, J.W. ApSimon, and A. Fruchier Tetrahedron Lett. 36 1995 1973
12. C.D. Boyle, and Y. Kishi Tetrahedron Lett. 36 1995 4579
13. T.R. Hoye, J.I. Jimenez, and W.T. Shier J. Am. Chem. Soc. 116 1994 9409
14. W.T. Shier, H.K. Abbas, and F.A. Badria Tetrahedron Lett. 36 1995 1571
15. G.K. Poch, R.G. Powell, R.D. Plattner, and D. Weisleder Tetrahedron Lett. 35 1994 7707
16. S.C. Bezuidenhout, W.C.A. Gelderblom, C.P. Gorstallman, R.M. Horak, W.F.O. Marasas, G. Spiteller, and R. Vleggaar Chem. Commun. 1998 743
17. W.C.A. Gelderblom, K. Jaskiewicz, W.F.O. Marasas, P.G. Thiel, R.M. Horak, R. Vleggaar, and N.P. Kriek J. Appl. Environ. Microbiol. 54 1998 1806
18. E. Wang, W.P. Norred, C.W. Bacon, R.T. Riley, and A.H. Merrill J. Biol. Chem. 266 1991 14486
19. Y. Shi, L.F. Peng, and Y. Kishi J. Org. Chem. 62 1997 5666
20. M.K. Gurjar, V. Rajendran, and B.V. Rao Tetrahedron Lett. 39 1998 3803
21. For the synthesis of the related AAL toxins, see: H. Oikawa, D. Yamawaki, T. Kagawa, and A. Ichihara Tetrahedron Lett. 40 1999 6621
22. C.L. Pereira, Y.H. Chen, and F.E. McDonald J. Am. Chem. Soc. 131 2009 6066
23. M. Prakesch, D. Gree, S. Chandrasekhar, and R. Gree Eur. J. Org. Chem. 2005 1221
24. A. Sharma, S. Gamre, and S. Chattopadhyay Tetrahedron Lett. 48 2007 3705
25. M. Venkataiah, P. Somaiah, G. Reddipalli, and N.W. Fadnavis Tetrahedron: Asymmetry 20 2009 2230
26. I.K. Mangion, and D.W.C. MacMillan J. Am. Chem. Soc. 127 2005 3696
27. G.N. Varseev, and M.E. Maier Org. Lett. 9 2007 1461
28. S.P. Brown, M.P. Brochu, C.J. Sinz, and D.W.C. MacMillian J. Am. Chem. Soc. 125 2003 10808
29. S. Chandrasekar, B. Mahipal, and M. Kavitha J. Org. Chem. 74 2009 9531
30. G. Zhong Angew. Chem., Int. Ed. 42 2003 4247
31. Y. Hayashi, J. Yamaguchi, K. Hibino, and M. Shoji Tetrahedron Lett. 44 2003 8293
32. Y. Nakayama, G. Biju Kumar, and Y. Kobayashi J. Org. Chem. 65 2000 707
33. S. Sommer, M. Kuhn, and H. Waldmann Adv. Synth. Catal. 350 2008 1736
34. D.C.J. Waalboer, H.A. van Kalkeren, M.C. Schaapman, F.L. van Delft, and F.P.J.T. Rutjes J. Org. Chem. 74 2009 8878
35. A. Ahmed, E.K. Hoegenauer, V.S. Enev, M. Hanbauer, H.E. Kaehlig Ohler, and J. Mulzer J. Org. Chem. 68 2003 3026
36. M. Scholl, S. Ding, C.W. Lee, and R.H. Grubbs Org. Lett. 1 1999 953
37. X. Guinchard, and E. Roulland Org. Lett. 11 2009 4700
38. C.J. Forsyth, X. Jianyan, S.T. Nguyen, I.A. Samdal, L.R. Briggs, T. Rundberget, M. Sandvik, and C.O. Miles J. Am. Chem. Soc. 128 2006 15114