Toward a total synthesis of keramamide B

Heterocycles

Volumn 61, Issue , 2003, Pages 23-29

  Shioiri, Takayuki ^a   Hughes, Robert John ^b  

^a MEIJO UNIVERSITY   (Japan)

^b NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KERAMAMIDE B; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0347022335     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-03-S24     Document Type: Article

References (29)

1. (a) J. Kobayashi, F. Itagaki, H. Shigemori, M. Ishibashi, K. Takahashi, M. Ogura, S. Nagasawa, T. Nakamura, H. Hirota, T. Ohta, and S. Nozoe, J. Am. Chem. Soc., 1991, 113, 7812.
2. (b) M. Tsuda, H. Ishiyama, K. Masuko, T. Takao, Y. Shimonishi, and J. Kobayashi, Tetrahedron, 1999, 55, 12543 and references therein.
3. (c) Orbiculamide A also belongs to the keramamide family: see, N. Fusetani, T. Sugawara, S. Matsunaga, and H. Hirota, J. Am. Chem. Soc., 1991, 113, 7811.
4. T. Shioiri and Y. Hamada, Synlett, 2001, 184.
5. For synthetic studies towards keramamides, see (a) J. A. Sowinski and P. L. Toogood, Tetrahedron Lett., 1995, 36, 67.
6. (b) J. A. Sowinski and P. L. Toogood, Chem. Commun., 1999, 981.
7. S. Takuma, Y. Hamada, and T. Shioiri, Chem. Pharm. Bull., 1982, 30, 3147 and references therein.
8. (a) E. M. Burgess, R. Harold, Jr., and E. A. Taylor, J. Org. Chem., 1973, 38, 26.
9. (b) J. F. Okonya, T. Kolasa, and M. J. Miller, J. Org. Chem., 1995, 60, 1932.
10. (c) P. Wipf and P. C. Fritch, J. Am. Chem. Soc., 1996, 118, 12358.
11. For reviews, see (d) C. Lamberth, J. Prakt. Chem., 2000, 342, 518
12. and (e) S. Khapli, S. Day, and D. Mal, J. Indian Inst. Sci., 2001, 81, 461.
13. (a) D. R. Williams, P. D. Lowder, Y.-G. Gu, and D. A. Brooks, Tetrahedron Lett., 1997, 38, 331.
14. (b) A. J. Phillips, Y. Uto, P. Wipf, M. J. Reno, and D. R. Williams, Org. Lett., 2000, 2, 1165.
15. 2 to the dehydrogenation of the oxazoline.
16. (a) Y. Hamada, M. Shibata, T. Sugiura, S. Kato, and T. Shioiri, J. Org. Chem., 1987, 52, 1252.
17. (b) T. Aoyama, N. Sonoda, M. Yamaguchi, K. Toriyama, A. Anzai, A. Ando, and T. Shioiri, Synlett, 1998, 35.
18. M. A. Blanchette, W. Choy, J. T. Davis, A. P. Essenfeld, S. Masamune, W. R. Roush, and T. Sakai, Tetrahedron Lett., 1984, 25, 2183.
19. The corresponding (Z)-isomer was also isolated in 3% yield.
20. U. Schmidt and S. Weinbrenner, Synthesis, 1996, 28.
21. In this particular case, the use of DEPC and BopCl (bis(2-oxo-3-oxazolidinylphosphinic chloride) failed to give any coupling product.
22. Incidentally, the di-Boc tryptophan derivative (3) and the trifluoroacetyl derivative (18) were respectively converted to the bromo-di-Boc derivative (34). Initial attempt to cleave the (Diagram presented) trifluoroacetyl group of the bromo derivative derived from 18 with base resulted in the decomposition.
23. (a) T. Shioiri, Y. Hamada, and F. Matsuura, Pure Applied Chem., 1994, 66, 2151 and references therein.
24. (b) J. Deng, Y. Hamada, T. Shioiri, S. Matsunaga, and N. Fusetani, Angew. Chem., Int. Ed. Engl., 1994, 33, 1729.
25. (c) T. Shioiri, Y. Hamada, and F. Matsuura, Tetrahedron, 1995, 51, 3939.
26. (d) J. Deng, Y. Hamada, and T. Shioiri, Tetrahedron Lett., 1996, 37, 2261.
27. (e) S. Sasaki, Y. Hamada, and T. Shioiri, Tetrahedron Lett., 1997, 38, 3013.
28. (f) H. Fujiwara, K. Tojiki, F. Yokokawa, and T. Shioiri, Peptide Science 1999, 2000, 123.
29. 2.