The practical synthesis of a novel and highly potent analogue of bryostatin

Journal of the American Chemical Society

Volumn 124, Issue 46, 2002, Pages 13648-13649

  Wender, Paul A ^a   Baryza, Jeremy L ^a   Bennett, Chad E ^a   Bi, F Christopher ^a   Brenner, Stacey E ^a   Clarke, Michael O ^a   Horan, Joshua C ^a   Kan, Cindy ^a   Lacôte, Emmanuel ^a   Lippa, Blaise ^a   Nell, Peter G ^a   Turner, Tim M ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BRYOSTATIN; BRYOSTATIN 1;

ARTICLE; CANCER INHIBITION; CHEMICAL REACTION; DRUG ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IMMUNE SYSTEM;

ANTINEOPLASTIC AGENTS; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; LACTONES; MACROLIDES; PROTEIN KINASE C; TUMOR CELLS, CULTURED;

EID: 0037146084     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027509+     Document Type: Article

References (30)

1. (a) Mutter, R.; Wills, M. Bioorg. Med. Chem. 2000, 8, 1841-1860.
2. (b) Pettit, G. R. J. Nat. Prod. 1996, 59, 812-821.
3. (a) Oz, H. S.; Hughes, W. T.; Rehg, J. E.; Thomas, E. K. Microb. Pathog. 2000, 29, 187-190.
4. (b) Scheid, C.; Prendiville, J.; Jayson, G.; Crowther, D.; Fox, B.; Pettit, G. R.; Stern, P. L. Cancer Immunol. Immunother. 1994, 39, 223-230.
5. (a) Al-Katib, A. M.; Smith, M. R.; Kamanda, W. S.; Pettit, G. R.; Hamdan, M.; Mohamed, A. N.; Chelladurai, B.; Mohammad, R. M. Clin. Cancer Res. 1998, 4, 1305-1314.
6. (b) Elgie, A. W.; Sargent, J. M.; Alton, P.; Peters, G. J.; Noordhuis, P.; Williamson, C. J.; Taylor, C. G. Leuk. Res. 1998, 22, 373-378.
7. (a) Mohammad, R. M.; Wall, N. R.; Dutcher, J. A.; Al-Katib, A. M. Clin. Cancer Res. 2000, 6, 4950-4956.
8. (b) Wang, S.; Wang, Z.; Boise, L. H.; Dent, P.; Grant, S. Leukemia 1999, 13, 1564-1573.
9. See: http://clinicaltrials.gov.
10. (a) Kazanietz, M. G. Mol. Pharm. 2002, 61, 759-767.
11. (b) Lorenzo, P. S.; Beheshti, M.; Pettit, G. R.; Stone, J. C.; Blumberg, P. M. Mol. Pharm. 2000, 57, 840-846.
12. (a) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Charette, A. B.; Prunet, J. A.; Lautens, M. J. Am. Chem. Soc. 1999, 121, 7540-7552.
13. (b) Kageyama, M.; Tamura, T.; Nantz, M. H.; Roberts, J. C.; Somfai, P.; Whritenour, D. C.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7407-7408.
14. (c) Ohmori, K.; Ogawa, Y.; Obitsu, T.; Ishikawa, Y.; Nishiyama, S.; Yamamura, S. Angew. Chem., Int. Ed. 2000, 39, 2290-2294.
15. (a) Wender, P. A.; Hinkle, K. W.; Koehler, M. F. T.; Lippa, B. Med. Res. Rev. 1999, 19, 388-407.
16. (b) Wender, P. A.; Martin-Cantalejo, Y.; Carpenter, A. J.; Chiu, A.; DeBrabander, J.; Harran, P. G.; Jimenez, J. M.; Koehler, M. F. T.; Lippa, B.; Morrison, J. A.; Muller, S. G.; Muller, S. N.; Park, C. M.; Shiozaki, M.; Siedenbiedel, C.; Skalitzky, D. J.; Tanaka, M.; Irie, K. Pure Appl. Chem. 1998, 70, 539-546.
17. (a) Wender, P. A.; DeBrabander, J.; Harran, P. G.; Jimenez, J. M.; Koehler, M. F. T.; Lippa, B.; Park, C. M.; Shiozaki, M. J. Am. Chem. Soc. 1998, 120, 4534-4535.
18. (b) Wender, P. A.; DeBrabander, J.; Harran, P. G.; Jimenez, J. M.; Koehler, M. F. T.; Lippa, B.; Park, C. M.; Siedenbiedel, C.; Pettit, G. R. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 6624-6629.
19. Wender, P. A.; Cribbs, C. M.; Koehler, K. F.; Sharkey, N. A.; Herald, C. L.; Kamano, Y.; Pettit, G. R.; Blumberg, P. M. Proc. Nat. Acad. Sci. U.S.A. 1988, 85, 7197-7201.
20. Aldrich 12.658-6, 3 kg = $38.40.
21. Cahiez, G.; Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1978, 3013-3014.
22. (a) Keck, G. E.; Krishnamurthy, D. Org. Synth. 1998, 75, 12-18.
23. (b) Yu, C. M.; Choi, H. S.; Yoon, S. K.; Jung, W. H. Synlett 1997, 889-890.
24. 19F NMR analysis of the Mosher ester of 5.
25. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
26. Viscontini, M.; Ebnöther, C. Helv. Chim. Acta 1951, 34, 116-117.
27. (a) Harada, T.; Inoue, A.; Wada, I.; Uchimura, J.; Tanaka, S.; Oku, A. J. Am. Chem. Soc. 1993, 115, 7665-7674.
28. (b) Mouné, S.; Niel, G.; Busquet, M.; Eggleston, I.; Jouin, P. J. Org. Chem. 1997, 62, 3332-3339.
29. Joly, G. D.; Jacobsen, E. N. Org. Lett. 2002, 4, 1795-1798.
30. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.