Asymmetric total synthesis of (+)-fostriecin

Organic Letters

Volumn 4, Issue 6, 2002, Pages 969-971

  Reddy, Y Krishna ^a   Falck, J R ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ENZYME INHIBITOR; FOSTRIECIN; PHOSPHOPROTEIN PHOSPHATASE; PYRONE DERIVATIVE;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; SYNTHESIS;

ALKENES; ENZYME INHIBITORS; PHOSPHOPROTEIN PHOSPHATASE; PYRONES;

EID: 0037149632     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025537r     Document Type: Article

References (29)

1. (a) Tunac, J. B.; Graham, B. D.; Dobson, W. E. J. Antibiot. 1983, 36, 1595-1600.
2. (b) Stampwala, S. S.; Bunge, R. H.; Hurley, T. R.; Willmer, N. E.; Brankiewicz, A. J.; Steinman, C. E.; Smitka, T. A.; French, J. C. J. Antibiot. 1983, 36, 1601-1605.
3. (a) Review: Murray, A. W. Nature 1992, 359, 599-604.
4. (b) De Jong, R. S.; De Vries, E. G. E.; Mulder, N. H. Anti-Cancer Drugs 1997, 8, 413-418.
5. Boritzki, T. J.; Wolfard, T. S.; Besserer, J. A.; Jackson, R. C.; Fry, D. W. Biochem. Pharmacol. 1988, 37, 4063-4068.
6. Walsh, A. H.; Cheng, A.; Honkanen, R. E. FEBS Lett. 1997, 416, 230-234.
7. Hastie, C. J.; Cohen, P. T. W. FEBS Lett. 1998, 431, 357-361.
8. Weinbrenner, C.; Baines, C. P.; Liu, G.-S.; Armstrong, S. C.; Ganote, C. E.; Walsh, A. H.; Honkanen, R. E.; Cohen, M. V.; Downey, J. M. Circulation 1998, 98, 899-905.
9. Armstrong, S. C.; Gao, W.; Lane, J. R.; Ganote, C. E. J. Mol. Cell. Cardiol. 1998, 30, 61-73.
10. Hokanson, G. C.; French, J. C. J. Org. Chem. 1985, 50, 462-466.
11. Boger, D. L.; Hikota, M.; Lewis, B. M. J. Org. Chem. 1997, 62, 1748-1753.
12. Boger, D. L.; Ichikawa, S.; Zhong, W. J. Am. Chem. Soc. 2001, 123, 4161-4167.
13. Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2001, 40, 3667-3670.
14. Other synthetic studies directed toward 1: (a) Just, G.; O'Connor, B. Tetrahedron Lett. 1988, 29, 753-756.
15. (b) Cossy, J.; Pradaux, F.; BouzBouz, S. Org. Lett. 2001, 3, 2233-2235.
16. Clinical trials were halted early due to concerns over the stability and purity of 1: De Jong, R. S.; Mulder, N. H.; Uges, D. R. A.; Sleijfer, D. T.; Hoppener, F. J. P.; Groen, H. J. M.; Willemse, P. H. B.; Van der Graaf, W. T. A.; De Vries, E. G. E. Br. J. Cancer 1999, 79, 882-887.
17. Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092-2093.
18. Bertus, P.; Pale, P. Tetrahedron Lett. 1997, 38, 8193-8196.
19. (a) Smith, A. B., III.; Ott, G. R. J. Am. Chem. Soc. 1998, 120, 3935-3948.
20. (b) Glanzer, B. I.; Faber, K.; Griengl, H. Tetrahedron 1987, 43, 5791-5796.
21. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
22. Hofmeister, H.; Annen, K.; Laurent, H.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1984, 23, 727-729.
23. Duffault, J.-M.; Einhorn, J.; Alexakis, A. Tetrahedron Lett. 1991, 32, 3701-3704.
24. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
25. Gautier, E. C. L.; Graham, A. E.; McKillop, A.; Standen, S. P.; Taylor, R. J. K. Tetrahedron Lett. 1997, 38, 1881-1884.
26. Rama Rao, A. V.; Reddy, E. R.; Sharma, G. V. M.; Yadagiri, P.; Yadav, J. S. Tetrahedron Lett. 1985, 26, 465-468.
27. Ohmura, T.; Yamamoto, Y.; Miyaura, N. J. Am. Chem. Soc. 2000, 122, 4990-4991.
28. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
29. Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434-9453.