Bromoetherification-based strategy towards the spirocyclic chromophore of chlorofusin

Tetrahedron Letters

Volumn 47, Issue 25, 2006, Pages 4171-4174

  Wei, Wan Guo ^a   Qian, Wen Jian ^a   Zhang, Yong Xia ^a   Yao, Zhu Jun ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; BROMINE DERIVATIVE; CHLOROFUSIN; KETONE DERIVATIVE; PROTEIN INHIBITOR; PROTEIN MDM2; PROTEIN P53; SILVER NITRATE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHROMATOPHORE; ETHERIFICATION; OXIDATION; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 33646521935     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.062     Document Type: Article

References (49)

1. Lane D.P. Nature 358 (1992) 15
2. Chen J.-D., Wu X.-W., Lin J.-Y., and Levine A.-J. Mol. Cell. Biol. 16 (1996) 2445
3. Hollstein M., Rice K., Greenblatt M.S., Soussi T., Fuchs R., Sorlie T., Hovig E., Smithsorensen B., Montesano R., and Harris C.C. Nucleic Acids Res. 22 (1994) 3551
4. Levine A.J., Momand J., and Finlay C.A. Nature 351 (1991) 453
5. Momand J., Zambetti G.P., Olson D.C., George D., and Levine A.J. Cell 69 (1992) 1237
6. Blommers M.J.J., Fendrich G., Garcia-Echeverria C., and Chène P. J. Am. Chem. Soc. 119 (1997) 3425
7. Freedman D.A., Wu L., and Levine A. J. Cell Mol. Life Sci. 55 (1999) 96
8. Jones S.N., Roe A.E., Donehower L.A., and Bradley A. Nature 378 (1995) 206
9. Juven-Gershon T., and Oren M. Mol. Med. 5 (1999) 71
10. Chène P. Nat. Rev. Cancer 3 (2003) 102
11. Fischer P.M., and Lane D.P. Trends Pharmacol. Sci. 25 (2004) 343
12. Duncan S.J., Gruschow S., Williams D.H., McNicholas C., Purewal R., Hajek M., Geritz M., Martin S., Wrigley S.V., and Moore M. J. Am. Chem. Soc. 123 (2001) 554-560
13. Duncan S.J., Gruschow S., Williams D.H., McNicholas C., Purewal R., Hajek M., Geritz M., Martin S., Wrigley S.V., and Moore M. J. Am. Chem. Soc. 124 (2002) 14503
14. Duncan S.J., Cooper M.A., and Williams D.H. Chem. Commun. (2003) 316-317
15. Boger D.L., Desharnais J., and Capps K. Angew. Chem., Int. Ed. 42 (2003) 4138
16. Zheleva D.I., Lane D.P., and Fischer P.M. Mini-Rev. Med. Chem. 3 (2003) 257
17. Desai P., Pfeiffer S.S., and Boger D.L. Org. Lett. 5 (2003) 5047
18. Malkinson J.P., Zloh M., Kadom M., Errington R., Smith P.J., and Searcey M. Org. Lett. 5 (2003) 5051
19. Closs A., and Hauser D. Helv. Chim. Acta. 56 (1973) 276
20. Natsume M., Takahashi Y., and Marumo S. Agric. Biol. Chem. 52 (1988) 307
21. Tomoda H., Matsushima C., Tabata N., Namatame I., Tanaka H., Bamberger M.J., Arai H., Fukazawa M., Inoue K., and Omura S. J. Antibiot. 52 (1999) 160
22. Coghlan D.R., Mackintosh J.A., and Karuso P. Org. Lett. 7 (2005) 2401
23. Wei W.-G., and Yao Z.-J. J. Org. Chem. 70 (2005) 4585
24. Wei W.G., and Yao Z.J. Tetrahedron 69 (2003) 6621
25. Naturally occurring azaphilones, see:. Itabashi T., Nozawa K., Nakajima S., and Kawai K.-I. Chem. Pharm. Bull. 4 (1993) 2040
26. Hashimoto T., Tahara S., Takaoka S., Tori M., and Asakawa Y. Chem. Pharm. Bull. 42 (1994) 2397
27. Nozawa K., Saito R., Udagawa S.-I., Nakajima S., and Kawai K.-I. Phytochemistry 39 (1995) 719
28. Yoshida E., Fujimoto H., and Yamazaki M. Chem. Pharm. Bull. 44 (1996) 284
29. Thines E., Anke H., and Sterner O. J. Nat. Prod. 61 (1998) 306
30. Suzuki S., Hosoe T., Nozawa K., Yaguchi T., Udagawa S.-I., and Kawai K.-I. J. Nat. Prod. 62 (1999) 1328
31. Kono K., Tanaka M., Ono Y., Hosoya T., Ogita T., and Kohama T. J. Antibiot. 54 (2001) 415
32. Michael A.P., Grace E.J., Kotiw M., and Barrow R.A. Aust. J. Chem. 56 (2003) 13
33. Laakso J.A., Raulli R., McElhaney-Feser G.E., Actor P., Underiner T.L., Hotovec B.J., Mocek U., Cihlar R.L., and Broedel Jr. S.E. J. Nat. Prod. 66 (2003) 1041
34. Bell P.J.L., and Karuso P. J. Am. Chem. Soc. 125 (2003) 9304
35. Quang D.N., Hashimoto T., Tanaka M., Stadler M., and Asakawa Y. Phytochemistry 65 (2004) 469
36. Quang D.N., Hashimoto T., Fournier J., Stadler M., Radulović N., and Asakawa Y. Tetrahedron 61 (2005) 1743
37. Chong R., King R.R., and Whalley W.B. J. Chem. Soc. C (1971) 3566
38. Chong R., King R.R., and Whalley W.B. J. Chem. Soc. C (1971) 3571
39. Suzuki T., Okada C., Arai K., Awall A., Shimizu T., Tanemura K., and Horaguchi T. J. Heterocycl. Chem. 38 (2001) 1409
40. Kamino T., Murata Y., Kawai N., Hosokawa S., and Kobayashi S. Tetrahedron Lett. 42 (2001) 5249
41. Zhu J.-L., Germain A.R., and Porco Jr. J.A. Angew. Chem., Int. Ed. 43 (2004) 1239
42. Zhu J.-L., Grigoriadis N.P., Lee J.P., and Porco Jr. J.A. J. Am. Chem. Soc. 127 (2005) 9342
43. Wei W.-G., Zhang Y.-X., and Yao Z.-J. Tetrahedron 61 (2005) 11882 and the references cited therein
44. For a prior reported related haloetherification-ring expansion, see:. Fujioka H., Ohba Y., Hirose H., Murai K., and Kita Y. Angew. Chem., Int. Ed. 44 (2005) 734
45. Chandrasekhar S., and Sridhar M. Tetrahedron Lett. 41 (2000) 5423 and the references cited therein
46. +): 406.1028; found, 406.1043.
47. +): 406.1028; found, 406.1041.
48. +): 406.1028; found, 406.1028.
49. +): 406.1028; found, 406.1027.