Total Synthesis of Spiruchostatin A, a Potent Histone Deacetylase Inhibitor

Journal of the American Chemical Society

Volumn 126, Issue 4, 2004, Pages 1030-1031

  Yurek George, Alexander ^a   Habens, Fay ^b   Brimmell, Matthew ^b   Packham, Graham ^b   Ganesan, A ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DISULFIDE; DNA; FR 901228; HISTONE DEACETYLASE INHIBITOR; HYDROXAMIC ACID; LYSINE; PRODRUG; PROTEIN; SPIRUCHOSTATIN A; TRAPOXIN B4; TRICHOSTATIN A; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CANCER; CATALYSIS; CLINICAL TRIAL; DRUG ACETYLATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME SUBSTRATE; EUKARYOTE; GENETIC TRANSCRIPTION; HUMAN; HYDROLYSIS; METAL BINDING; NUCLEOSOME; PROTON TRANSPORT; REDUCTION; REGULATORY MECHANISM; STRUCTURE ACTIVITY RELATION;

ENZYME INHIBITORS; HISTONE DEACETYLASES; PEPTIDES, CYCLIC; PSEUDOMONAS;

EID: 0942265466     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039258q     Document Type: Article

References (25)

1. Recent reviews: (a) Grozinger, C. M.; Schreiber, S. L. Chem. Biol. 2002, 9, 3-16.
2. (b) Marks, P. A.; Miller, T.; Richon, V. M. Curr. Opin. Pharmacol. 2003, 3, 344-351.
3. (c) Miller, T. A.; Witter, D. J.; Belvedere, S. J. Med. Chem. 2003, 46, 5097-5116.
4. (a) Yoshida, M.; Kijama, M.; Akita, M.; Beppu, T. J. Biol. Chem. 1990, 265, 17174-17179.
5. (b) Yoshida, M.; Hoshikawa, Y.; Koseki, K.; Mori, K.; Beppu, T. J. Antibiot. 1990, 43, 1101-1106.
6. Richon, V. M.; Emiliani, S.; Verdin, E.; Webb, Y.; Breslow, R.; Rifkind, R. A.; Marks, P. A. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 3003-3007.
7. (a) Kijama, M.; Yoshida, M.; Sugita, K.; Horinouchi, S.; Beppu, T. J. Biol. Chem. 1993, 268, 22429-22435.
8. (b) Taunton, J.; Collins, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1996, 118, 10412-10422.
9. (a) Ueda, H.; Nakajima, H.; Hori, Y.; Fujita, T.; Nishimura, M.; Goto, T.; Okuhara, M. J. Antibiot. 1994, 47, 301-310.
10. (b) Shigematsu, N.; Ueda, H.; Takase, S.; Tanaka, H.; Yamamoto, K.; Tada, T. J. Antibiot. 1994, 47, 311-314.
11. (c) Ueda, H.; Manda, T.; Matsumoto, S.; Mukumoto, S.; Nishigaki, F.; Kawamura, I.; Shimomura, K. J. Antibiot. 1994, 47, 315-323.
12. Furumai, R.; Matsuyama, A.; Kobashi, N.; Lee, K.-H.; Nishiyama, N.; Nakajima, H.; Tanaka, A.; Komatsu, Y.; Nishino, N.; Yoshida, M.; Horinouchi, S. Cancer Res. 2002, 62, 4916-4921.
13. Li, K. W.; Xing, W.; Simon, J. A. J. Am. Chem. Soc. 1996, 118, 7237-7238.
14. (a) Shin-ya, K.; Masuoka, Y.; Nagai, A.; Furihata, K.; Nagai, K.; Suzuki, K.; Hayakawa, Y.; Seto, Y. Tetrahedron Lett. 2001, 42, 41-44.
15. (b) Shinya, K., personal communication.
16. Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837-8838.
17. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364.
18. (a) Nagao, Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue, T.; Hashimoto, K.; Fujita, E. J. Org. Chem. 1986, 51, 2391-2393.
19. (b) Review: Velazquez, F.; Olivo, H. F. Curr. Org. Chem. 2002, 6, 303-340.
20. Aiguadé, J.; González, A.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952.
21. Chen, Y.; Gambs, C.; Abe, Y.; Wentworth, P., Jr.; Janda, K. D. J. Org. Chem. 2003, 68, 8902-8905.
22. Liang, B.; Richard, D. J.; Portonovo, P.; Jouillié, M. M. J. Am. Chem. Soc. 2001, 123, 4469-4474.
23. Cosp, A.; Romea, P.; Talavera, P.; Urpí, F.; Vilarrasa, J.; Font-Bardia, M.; Solans, X. Org. Lett. 2001, 3, 615-617.
24. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
25. Kamber, B.; Hartmann, A.; Eisler, K.; Riniker, B.; Rink, H.; Sieber, P.; Rittel, W. Helv. Chim. Acta 1980, 63, 899-915.