Synthesis and biological activities of sugar analogs of mycalamide A

Heterocycles

Volumn 69, Issue 1, 2006, Pages 487-495

  Takahashi, Shunya ^a   Okada, Akihiro ^a   Nishiwaki, Miho ^a   Nakata, Tadashi ^b  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947243304     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-06-s(o)35     Document Type: Article

References (47)

1. Perry N.B., Blunt J.W., Munro M.H.G., and Pannell L.K. J. Am. Chem. Soc. 110 (1988) 4850
2. Perry N.B., Blunt J.W., Munro M.H.G., and Thompson A.M. J. Org. Chem. 55 (1990) 223
3. West L.M., Northcote P.T., Hood K.A., Miller J.H., and Page M.J. J. Nat. Prod. 63 (2000) 707
4. Sakemi S., Ichiba T., Kohmoto S., Saucy G., and Higa T. J. Am. Chem. Soc. 110 (1988) 4851
5. Matsunaga S., Fusetani N., and Nakao Y. Tetrahedron 48 (1992) 8369
6. Kobayashi J., Itagaki F., Shigemori H., and Sasaki T. J. Nat. Prod. 56 (1993) 976
7. Fusetani N., Sugawara T., and Matsunaga S. J. Org. Chem. 57 (1992) 3828
8. Paul G.K., Gunasekera S.P., Longley R.E., and Pomponi S.A. J. Nat. Prod. 65 (2002) 59
9. Burres N.S., and Clement J.J. J. Cancer Res. 49 (1989) 2935
10. Ogawara H., Higashi K., Uchino K., and Perry N.B. Chem. Pharm. Bull. 39 (1991) 2152
11. Galvin F., Freeman G.J., Razi-Wolf Z., Benacerraf B., Nadler L., and Reiser H. Eur. J. Immunol. 23 (1993) 283
12. Hong C.Y., and Kishi Y. J. Org. Chem. 55 (1990) 4242
13. Hong C.Y., and Kishi Y. J. Am. Chem. Soc. 113 (1991) 9693
14. Nakata T., Matsukura H., Jian D.L., and Nagashima H. Tetrahedron Lett. 35 (1994) 8229
15. Nakata T., Fukui H., Nakagawa T., and Matsukura H. Heterocycles 42 (1996) 159
16. Trotter N.S., Takahashi S., and Nakata T. Org. Lett. 1 (1999) 957
17. Kocienski P., Raubo P., Davis J.K., Boyle F.T., Davies D.E., and Richter A. J. Chem. Soc., Perkin Trans. 1 (1996) 1797
18. Kocienski P.J., Narquizian R., Raubo P., Smith C., and Boyle F.T. Synlett (1998) 869
19. Kocienski P.J., Narquizian R., Raubo P., Smith C., and Boyle F.T. Synlett (1998) 1432
20. Kocienski P., Narquizian R., Raubo P., Smith C., Farrugia L.J., Muir K., and Boyle F.T. J. Chem. Soc., Perkin Trans. 1 (2000) 2357
21. Roush W.R., and Marron T.G. Tetrahedron Lett. 34 (1993) 5421
22. Roush W.R., Marron T.G., and Pfeifer L.A. J. Org. Chem. 62 (1997) 474
23. Marron T.G., and Roush W.R. Tetrahedron Len. 36 (1995) 1581
24. Roush W.R., Pfeifer L.A., and Marron T.G. J. Org. Chem. 63 (1998) 2064
25. Roush W.R., and Pfeifer L.A. Org. Lett. 2 (2000) 859
26. Trost B.M., Yang H., and Probst G.D. J. Am. Chem. Soc. 126 (2004) 48
27. Sohn J.-H., Waizumi N., Zhong H.M., and Rawal V.H. J. Am. Chem. Soc. 127 (2005) 7290
28. Toyota M., Nishikawa Y., and Fukumoto K. Heterocycles 47 (1998) 675
29. Toyota M., Hirota M., Nishikawa Y., Fukumoto K., and Ihara M. J. Org. Chem. 63 (1998) 5895
30. Toyota M., Hirota M., Hirano H., and Ihara M. Org. Lett. 2 (2000) 2031
31. Rudyanto M., Toyota M., Kagawa N., and Ihara M. Heterocycles 58 (2002) 655
32. Kagawa N., Ihara M., and Toyota M. Org. Lett. 8 (2006) 875
33. Hoffmann R.W., and Schlapbach A. Tetrahedron Lett. 34 (1993) 7903
34. Hoffmann R.W., Breitfelder S., and Schlapbach A. Helv. Chim. Acta 79 (1996) 346
35. Breitfelder S., Schuemacher A.C., Roelle T., Kikuchi M., and Hoffmann R.W. Helv. Chim. Acta 87 (2004) 1202
36. Thompson A.M., Blunt J.W., Munro M.H.G., Perry N.B., and Pannel L.K. J. Chem. Soc., Perkin Trans. 1 (1992) 1335
37. Thompson A.M., Blunt J.W., Munro M.H.G., and Clark B.M. J. Chem. Soc., Perkin Trans. 1 (1994) 1025
38. Thompson A.M., Blunt J.W., Munro M.H.G., and Perry N.B. J. Chem. Soc., Perkin Trans. 1 (1995) 1233
39. Abell A.D., Blunt J.W., Foulds G.J., and Munro M.H.G. J. Chem. Soc., Perkin Trans. 1 (1997) 1647
40. Fukui H., Tsuchiya Y., Fujita K., Nakagawa T., Koshino H., and Nakata T. Bioorg. Med. Chem. Lett. 7 (1997) 2081
41. Takahashi S., Okada A., and Nakata T. Heterocycles 63 (2004) 2111
42. Potter A.L., Sowden J.C., Hassid W.Z., and Doudoroff M. J. Am. Chem. Soc. 70 (1948) 1751
43. Y. Narkajima and N. Yoneshima, Jpn. Kokai Tokkyo Koho Jpn. Pat. 02069494, Mar 8, 1990.
44. A considerable amount (-20%) of the corresponding β-isomer was also formed.
45. Ikehara M., and Tada H. Chem. Pharm. Bull. 11 (1963) 1102
46. Paulsen H., Gyorgydeak Z., and Friedmann M. Chem. Ber. 107 (1974) 1590
47. Although NOE experiments were attempted, no useful information concerning the conformation of these analogs was obtained.