Total synthesis and conformational studies of ceratospongamide, a bioactive cyclic heptapeptide from marine origin

Tetrahedron

Volumn 58, Issue 40, 2002, Pages 8127-8143

  Yokokawa, Fumiaki ^a,c   Sameshima, Hirofumi ^a   In, Yasuko ^b   Minoura, Katsuhiko ^b   Ishida, Toshimasa ^b   Shioiri, Takayuki ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

^b OSAKA MEDICAL COLLEGE   (Japan)

^c Tsukuba Research Institute   (Japan)

Author keywords

Cis,cis ceratospongamide; Conformation; Synthesis; Thermodynamic isomerization; Trans,trans D allo Ile ceratospongamide

Indexed keywords

ANTIINFLAMMATORY AGENT; CERATOSPONGAMIDE; DIMETHYL SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CIS ISOMER; DRUG CONFORMATION; DRUG SYNTHESIS; PRIORITY JOURNAL; SIMULATION; STRUCTURE ANALYSIS; TRANS ISOMER; X RAY CRYSTALLOGRAPHY;

EID: 0037201507     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00906-7     Document Type: Article

References (37)

1. Kucuk O., Young M.L., Habermann T.M., Wolf B.C., Jimeno J., Cassileth P.A. Am. J. Clin. Oncol. 23:2000;273-277.
2. Madden T., Tran H.T., Beck D., Huie R., Newman R.A., Pusztai L., Wright J.J., Abbruzzese J.L. Clin. Cancer Res. 6:2000;1293-1301.
3. Hochster H., Oratz R., Ettinger D.S., Borden E. Invest. New Drugs. 16:1999;259-263.
4. Grabley S., Thiericke R. Adv. Biochem. Engng Biotechnol. 64:1999;101-154.
5. (a) Wipf P. Chem. Rev. 95:1995;2115-2134.
6. (b) Shioiri T., Hamada Y. Synlett. 2001;184-201.
7. Wipf P., Fritch P.C., Geib S.J., Sefler A.M. J. Am. Chem. Soc. 120:1998;4105-4112.
8. Tan L.T., Williamson R.T., Gerwick W.H., Watts K.S., McGough K., Jacobs R. J. Org. Chem. 65:2000;419-425.
9. . A part of this work was preliminary reported. See Yokokawa F., Sameshima H., Shioiri T. Synlett. SI:2001;986-988.
10. Shioiri T., Hamada Y. Atta-ur-Rahman, . Studies in Natural Products Chemistry. Vol. 4:1989;83-110 Elsevier, Amsterdam. Part C.
11. (a) Hamada Y., Shibata M., Sugiura T., Kato S., Shioiri T. J. Org. Chem. 52:1987;1252-1255.
12. (b) Aoyama T., Sonoda N., Yamauchi M., Toriyama K., Anzai A., Ando A., Shioiri T. Synlett. 1998;35-36.
13. (c) Fujiwara H., Tojiki K., Yokokawa F., Shioiri T. Pept. Sci. 1999:2000;9-12.
14. (d) Sugiyama H., Yokokawa F., Shioiri T. Org. Lett. 2:2000;2149-2152.
15. Takuma S., Hamada Y., Shioiri T. Chem. Pharm. Bull. 30:1982;3147-3153. and references therein.
16. The Weinreb amide 10 is currently commercially available from Aldrich.
17. Fehrentz J.-A., Castro B. Synthesis. 1983;676-678.
18. Shioiri T., Ninomiya K., Yamada S. J. Am. Chem. Soc. 94:1972;6203-6205.
19. (a) Chen S., Xu J. Tetrahedron Lett. 32:1991;6711-6714.
20. (b) Dudash J. Jr., Jiang J., Mayer S.C., Joullie M.M. Synth. Commun. 23:1993;349-356.
21. (c) Deng J., Hamada Y., Shioiri T., Matsunaga S., Fusetani N. Angew. Chem. Int. Ed. Engl. 33:1994;1729-1731.
22. (d) Deng J., Hamada Y., Shioiri T. Synthesis. 1998;627-638.
23. Ehrlich A., Heyne H.-U., Winter R., Beyermann M., Haber H., Carpino L.A., Bienert M. J. Org. Chem. 61:1996;8831-8838.
24. Phillips A.D., Uto Y., Wipf P., Reno M.J., Williams D.R. Org. Lett. 2:2000;1165-1168.
25. (a) X-Ray and thermal isomerization works were presented at 36th Tennenbutsu Danwakai (Nagoya, Japan), July 15-17, 2001 and at 18th International Congress of Heterocyclic Chemistry (Yokohama, Japan), July 29-August 3, 2001; Abstracts; p 124.
26. (a) X-Ray and thermal isomerization works were presented at 36th Tennenbutsu Danwakai (Nagoya, Japan), July 15-17, 2001 and at 18th International Congress of Heterocyclic Chemistry (Yokohama, Japan), July 29-August 3, 2001; Abstracts; p 124.
27. (b) Very recently, X-ray structure analysis of 1 was reported: Doi, M.; Yumiba, A.; Asano, A. Acta Crystallogr. 2002, E58, o62-o64.
28. Ishida T., Tanaka M., Nabae M., Inoue M., Kato S., Hamada Y., Shioiri T. J. Org. Chem. 53:1988;107-112.
29. Hossain M.B., van der Helm D., Antel J., Sheldrick G.M., Sanduja S.K., Weinheimer A.J. Proc. Natl Acad. Sci. USA. 85:1988;4118-4122.
30. Deng S., Taunton J. J. Am. Chem. Soc. 124:2002;916-917.
31. Siemion I.Z., Wieland T., Pook K. Angew. Chem. Int. Ed. Engl. 14:1975;702-703.
32. Sheldrick, G.M. SHELXS97. Program for the Solution of Crystal Structure; University of Gottingen: Germany, 1997.
33. Sheldrick, G. M. SHELXL97. Program for the Refinement of Crystal Structure; University of Gottingen: Germany, 1997.
34. Clore G.M., Nigles M., Sukumaran D.K., Bruenger A.T., Karplus M., Gronenborn A.M. EMBO J. 5:1986;2729-2735.
35. Nilges M., Clore G.M., Gronenborn A.M. FEBS Lett. 229:1988;317-324.
36. INSIGHT/DISCOVER; Biosym Technologies, Molecular Simulation Inc.: 9685 Scranton Road, San Diego, CA, USA.
37. Dauber-Osguthorpe P., Roberts V.A., Osguthorpe D.J., Wolff J., Genest M., Hagler A.T. Proteins Struct. Funct. Genet. 4:1988;31-47.