Synthetic approaches to the southern part of cyclotheonamide C

Tetrahedron Letters

Volumn 44, Issue 49, 2003, Pages 8827-8830

  Aitken, David J ^a   Faure, Sophie ^a   Roche, Stéphane ^a  

^a Univ Blaise Pascal Clermont F   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOTHEONAMIDE C; PALLADIUM; PENTAPEPTIDE; SERINE PROTEINASE INHIBITOR; THROMBIN INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG ISOLATION; DRUG SYNTHESIS; HECK REACTION; HORNER WADSWORTH EMMONS REACTION; ISOMERISM; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SPONGE (PORIFERA);

THEONELLA;

EID: 0242361244     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.196     Document Type: Article

References (36)

1. Fusetani N., Matsunaga S. J. Am. Chem. Soc. 112:1990;7053-7054.
2. Nakao Y., Matsunaga S., Fusetani N. Bioorg. Med. Chem. 3:1995;1115-1122.
3. Nakao Y., Oku N., Matsunaga S., Fusetani N. J. Nat. Prod. 61:1998;667-670.
4. Murakami Y., Takei M., Shindo K., Kitazume C., Tanaka J., Higa T., Fukamachi H. J. Nat. Prod. 65:2002;259-261.
5. Maryanoff B.E., Qiu X., Padmanabhan K.P., Tulinsky A., Almond H.R., Andrade-Gordon P., Greco M.N., Kauffman J.A., Nicolaou K.C., Liu A., Brungs P.H., Fusetani N. Proc. Natl. Acad. Sci. USA. 90:1993;8048-8052.
6. Lee A.Y., Hagihara M., Karmacharya R., Albers M.W., Schreiber S.L., Clardy J. J. Am. Chem. Soc. 115:1993;12619-12620.
7. Lin Z., Johnson M.E. Protein Peptide Lett. 1:1994;9-14.
8. Maryanoff B.E., Zhang H.-C., Greco M.N., Glover K.A., Kauffman J.A., Andrade-Gordon P. Bioorg. Med. Chem. 3:1995;1025-1038.
9. Ganesh V., Lee A.Y., Clardy J., Tulinsky A. Protein Sci. 5:1996;825-835.
10. Wipf P., Kim H. J. Org. Chem. 58:1993;5592-5594.
11. Maryanoff B.E., Greco M.N., Zhang H.-C., Andrade-Gordon P., Kauffman J.A., Nicolaou K.C., Liu A., Brungs P.H. J. Am. Chem. Soc. 117:1995;1225-1239.
12. Hagihara M., Schreiber S.L. J. Am. Chem. Soc. 114:1992;6570-6571.
13. Deng J., Hamada Y., Shioiri T., Matsunaga S., Fusetani N. Angew. Chem., Int. Ed. Engl. 33:1994;1729-1731.
14. Bastiaans H.M., van der Baan J.L., Ottenheijm C.J. Tetrahedron Lett. 36:1995;5963-5966.
15. Deng J., Hamada Y., Shioiri T. Tetrahedron Lett. 37:1996;2261-2264.
16. Bastiaans H.M., van der Baan J.L., Ottenheijm C.J. J. Org. Chem. 62:1997;3880-3889.
17. Wasserman H.H., Zhang R. Tetrahedron Lett. 43:2002;3743-3746.
18. Wasserman H.H., Zhang R. Tetrahedron. 58:2002;6277-6283.
19. Schmidt U., Lieberknecht A., Wild J. Synthesis. 1988;159-172.
20. Schmidt U., Griesser H., Leitenberger V., Lieberknecht A., Mangold R., Meyer R., Riedl B. Synthesis. 1992;487-490.
21. Akita H., Chen C.Y., Kato K. Tetrahedron. 54:1998;11011-11026.
22. Srinivasan A., Richards K.D., Olsen R.K. Tetrahedron Lett. 17:1976;891-894.
23. Carlström A.-S., Frejd T. Synthesis. 1989;414-418.
24. Zhu Y.-F., Yamazaki T., Tsang J.W., Lok S., Goodman M. J. Org. Chem. 57:1992;1074-1081.
25. For a review on the Heck reaction: Beletskaya I.P., Cheprakov A.V. Chem. Rev. 100:2000;3009-3066.
26. Herrmann W.A., Brossmer C., Reisinger C.-P., Riermeier T.H., Öfele K., Beller M. Chem. Eur. J. 3:1997;1357-1364.
27. For a review on the Suzuki reaction: Miyaura N., Suzuki A. Chem. Rev. 95:1995;2457-2483.
28. Campagne J.M., Prim D. Les complexes de palladium en synthèse organique: initiation et guide pratique. 2001;CNRS éditions, Paris.
29. Burk M.J., Allen J.G., Kiesman W.F., Stoffan K.M. Tetrahedron Lett. 38:1997;1309-1312.
30. De Koning C.B., Michael J.P., Rousseau A.L. J. Chem. Soc., Perkin Trans. 1. 2000;787-797.
31. Kristensen J., Lysén M., Vedsø P., Begtrup M. Org. Lett. 3:2001;1435-1437.
32. Zapf A., Beller M. Chem. Eur. J. 6:2000;1830-1833.
33. Semmelhack M.F., Schmid C.R., Cortés D.A., Chou C.S. J. Am. Chem. Soc. 106:1984;3374-3376.
34. Barrett A.G.M., Hamprecht D., Ohkubo M. J. Org. Chem. 62:1997;9376-9378.
35. Wei X., Taylor R.J.K. J. Org. Chem. 65:2000;616-620.
36. 6Si: C, 67.49; H, 8.09; N, 4.50. Found: C, 67.52; H, 8.09; N, 4.59.