Synthesis of linear tripeptides for right-hand segments of complestatin

Chemical and Pharmaceutical Bulletin

Volumn 53, Issue 10, 2005, Pages 1277-1290

  Yamada, Yaeko ^a   Akiba, Ai ^a   Arima, Shiho ^a   Okada, Chiharu ^a   Yoshida, Kiminari ^a   Itou, Fumihiro ^a   Kai, Toshitsugu ^a   Satou, Toshiko ^a   Takeda, Kazuyoshi ^b   Harigaya, Yoshihiro ^a  

^a KITASATO UNIVERSITY   (Japan)

^b EBARA CORPORATION   (Japan)

Author keywords

Complestatin; Precursor; Right hand segment; Tripeptide

Indexed keywords

COMPLESTATIN;

ARTICLE; DENSITY FUNCTIONAL THEORY; DRUG SYNTHESIS; ISOMERIZATION; RING CLOSING METATHESIS; SUZUKI REACTION;

CHLOROPHENOLS; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OLIGOPEPTIDES; PEPTIDES, CYCLIC; STEREOISOMERISM;

EID: 26444455582     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.53.1277     Document Type: Article

References (37)

1. Kaneko I., Fearon D. T., Austen K., J. Immunol., 124, 1194-1198 (1980).
2. Kaneko I., Kamoshida K., Takahashi S., J. Antibiot., 42, 236-241 (1989).
3. Seto H., Fujioka T., Furihata K., Kaneko I., Takahashi S., Tetrahedron Lett., 30, 4987-4990 (1989).
4. Matsuzaki K., Ikeda H., Ogino T., Matsumoto A., Woodruff H. B., Tanaka H., Omura S., J. Antibiot., 47, 1173-1174 (1994).
5. Gouda H., Matsuzaki K., Tanaka H., Hirono S., Omura S., MaCauley J. A., Sprengeler P. A., Furst G. T., Smith A. B., J. Am. Chem. Soc., 118, 13087-13088 (1996).
6. Jayasuriya H., Salituro G. M., Smith S. K., Heck J. V., Gould S. J., Singh S. B., Tetrahedron Lett., 39, 2247-2248 (1998).
7. Singh S. B., Jayasuriya H., Salituro G. M., Zink D. L., Shafee A., Heimbuch B., Silverman K. C., Lingham R. B., Genilloud O., Teran A., Vilella D., Felock P., Hazuda D., J. Nat. Prod., 64, 874-882 (2001).
8. Kai T., Kajimoto N., Konda (Yamada) Y., Harigaya Y., Takayanagi H., Tetrahedron Lett., 40, 6289-6292 (1999).
9. Deng H., Jung J.-K., Liu T., Kunz K. W., Snapper M. L., Hoveyda H., J. Am. Chem. Soc., 125, 9032-9034 (2003).
10. Suzuki A., Acc. Chem. Res., 15, 178-184 (19082).
11. Stille J. K., Pure Appl. Chem., 57, 1771-1780 (1985).
12. Konda-Yamada Y., Okada C., Yoshida K., Umeda Y., Arima S., Sato N., Kai T., Takayanagi H., Harigaya Y., Tetrahedron, 58, 7851-7861 (2002).
13. Irie K., Iguchi M., Oda T., Suzuki Y., Okuno S., Ohigashi H., Koshimizu K., Tetrahedron, 51, 6255-6266 (1995).
14. Inada A., Nakamura Y., Morita Y., Chem. Lett., 1980, 1287-1290 (1980).
15. Yokoyama Y., Hikawa H., Mitsuhashi M., Uyama A., Murakami M., Tetrahedron Lett., 44, 7803-7806 (1999).
16. Naruse N., Tenmyo O., Kobaru S., Hatori M., Tomita K., Hamagishi Y., Oki T., Careofokumura J., J. Antibiot., 46, 1804-1811 (1993).
17. Naruse N., Tenmyo O., Kobaru S., Hatori M., Tomita K., Hamagishi Y., Oki T., Careofokumura J., J. Antibiot., 46, 1812-1818 (1993).
18. Hobbs D. W., Still W. C., Tetrahedron Lett., 28, 2805-2808 (1987).
19. Crast L. B., Jr., U. S. Patent NO 3489750 (1970).
20. Wipf P., Yokokawa F., Tetrahedron Lett., 39, 2223-2226 (1998).
21. Farina V., Kapadia S., Krishnan B., Wang C., Liebeskind L. S., J. Org. Chem., 59, 5905-5911 (1994).
22. Littke A. F., Schwarz L., Fu G. C., J. Am. Chem. Soc., 124, 6343-6348 (2002).
23. Choussy M. B., Zhu J., J. Org. Chem., 63, 5662-5665 (1998).
24. Roussi G., Zamora E. G., Carbonnelle A. C., Beugelmans R., Heterocycles, 51, 2041-2063 (1991).
25. Roussi G., Zamora E. G., Carbonnelle A. C., Beugelmans R., Tetrahedron Lett., 38, 4401-4404 (1997).
26. Chevallent P., Grrouste P., Malawska B., Martinez J., Tetrahedron Lett., 34, 7409-7412 (1993).
27. Dourtoglou V., Gross B., Synthesis, 1984, 573-574 (1984).
28. Miyama N., Suzuki A., Chem. Rev., 95, 2457-2483 (1995).
29. Ishikawa T., Murata M., Miyaura N., J. Org. Chem., 60, 7508-7510 (1995).
30. Eider A. M., Rich D. H., Organic Lett., 1, 1443-1446 (1999).
31. Littke A. M., Schwarz L., Fu G. C., J. Am. Chem. Soc., 124, 6343-6348 (2002).
32. The thesis of Matsuzaki K., "Investigation of inhibitors of gp120-CD4 receptor having anti HIV activity produced from microorganism," 1997, p. 55.
33. Carbonnelle A. C., Zamora E. G., Beugelmans R., Roussi G., Tetrahedron Lett., 39, 4471-4472 (1998).
34. Spartan '04 for Windows; Wavefunction, Inc.; Irvine, CA, 2003.
35. Hehre W. J., A Guide to Molecular Mechanics and Quantum Chemical Calculations; Wavefunction, Inc.: Irvine, CA, 2003.
36. Lee C., Yang W., Parrr R. G., Phys. Rev., 37, 785-789 (1988).
37. Beck A. D., J. Chem. Phys., 98, 5648-5652 (1993).