Synthesis and biological evaluation of bryostatin analogues: The role of the A-ring

Tetrahedron Letters

Volumn 41, Issue 7, 2000, Pages 1007-1011

  Wender, Paul A ^a   Lippa, Blaise ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BRYOSTATIN; BRYOSTATIN DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL GROWTH; CHEMICAL BOND; CHEMICAL REACTION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ESTERIFICATION; GROWTH INHIBITION; LEUKEMIA CELL; MOUSE; NONHUMAN; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0034639714     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02195-4     Document Type: Article

References (22)

1. (a) Pettit, G. R.; Herald, C. L.; Doubek, D. L.; Herald, D. L.; Arnold, E.; Clardy, J. J. Am. Chem. Soc. 1982, 104, 6846-6848;
2. (b) Pettit, G. R. J. Nat. Prod. 1996, 59, 812-821;
3. (c) Wender, P. A.; Hinkle, K. W.; Koehler, M. F. T.; Lippa, B. Med. Res. Rev. 1999, 19, 388-407.
4. (a) Varterasian, M.; Mohammad, R.; Shurafa, M.; Eilender, D.; Murgo, A.; Hulburd, K.; Rodriguez, D.; Pemberton, P.; Lagrone, F.; Manica, B.; Spadoni, V.; Alkatib, A. Blood 1998, 92 (#10/ pt.1/S1), 1702;
5. (b) Philip, P. A.; Rea, D.; Thavasu, P.; Carmichael, J.; Stuart, N. S. A.; Rochett, H.; Talbot, D. C.; Ganesan, T.; Pettit, G. R.; Balkwill, F.; Harris, A. L. J. Natl. Cancer Inst. 1993, 85, 1812-1818.
6. (a) Kraft, A. S.; Smith, J. B.; Berkow, R. L. Proc. Natl. Acad. Sci. USA 1986, 83, 1334-1338.
7. (b) Berkow, R. L.; Kraft, A. S. Biochem. Biophys. Res. Commun. 1985, 131, 1109-1116.
8. (c) Ramsdell, J. S.; Pettit, G. R.; Tashjian Jr., A. H. J. Biol. Chem. 1986, 261, 17073-17080.
9. Kraft, A. S.; Woodley, S.; Pettit, G. R.; Gao, F.; Coll, J. C.; Wagner, F. Cancer Chemother. Pharmacol. 1996, 37, 271-278.
10. (a) Maki, A.; Diwakaran, H.; Redman, B.; Alasfar, S.; Pettit, G. R.; Mohammad, R. M.; Alkatib, A. Anti-Cancer Drugs 1995, 6, 392-397;
11. (b) Mohammad, R. M.; Diwakaran, H.; Maki, A.; Emara, M. A.; Pettit, G. R.; Redman, B.; Alkatib, A. Leuk. Res. 1995, 19, 667-673.
12. Alkatib, A.; Mohammad, R. M.; Dan, M.; Hussein, M. E.; Akhtar, A.; Pettit, G. R.; Sensenbrenner, L. L. Exp. Hematol. 1993, 21, 61-65.
13. Two total syntheses of a bryostatin have been completed to date: (a) 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; (b) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2354-2359.
14. Two total syntheses of a bryostatin have been completed to date: (a) 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; (b) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2354-2359.
15. (a) Wender, P. A.; De Brabander, J.; Harran, P. G.; Jimenez, J.-M.; Koehler, M. F. T.; Lippa, B.; Park, C. M.; Siedenbiedel, C.; Pettit, G. R. J. Am. Chem. Soc. 1998, 120, 4534-4535;
16. (b) Wender, P. A.; De Brabander, 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. USA 1998, 55, 6624-6631;
17. (c) Wender, P. A.; De Brabander, J.; Harran, P. G.; Hinkle, K. W.; Lippa, B.; Pettit, G. R. Tetrahedron Lett. 1998, 39, 8625-8628.
18. Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831-1833.
19. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
20. Theisen, P. D.; Heathcock, C. H. J. Org. Chem. 1988, 53, 2374-2378.
21. Binding assays were carried out on a PKC isozyme mix purified from rat brain, see: Ref. 8b for details.
22. Cornelis, B.; Glaudemans, P. J.; Bertolini, M. J. In Methods in Carbohydrate Chemistry; Whistler, R. L.; Bemiller, J. N., Eds.; Academic Press: San Francisco, 1980; Vol. VIII, pp. 271-275.