Synthesis of tripeptide hydrolysate from papuamide A: Determination of absolute stereostructure of β-methoxytyrosine

Tetrahedron Letters

Volumn 46, Issue 40, 2005, Pages 6827-6830

  Makino, Kazuishi ^a   Nagata, Eri ^a   Hamada, Yasumasa ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Absolute stereochemistry; Papuamide A; Relative stereochemistry; Methoxytyrosine

Indexed keywords

CYCLODEPSIPEPTIDE; PAPUAMIDE A; PROTEIN HYDROLYSATE; TRIPEPTIDE DERIVATIVE; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASSAY; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

EID: 27744514295     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.08.023     Document Type: Article

References (24)

1. Ford, P. W.; Gustafson, K. R.; McKee, T. C.; Shigematsu, N.; Maurizi, L. K.; Pannell, L. K.; Williams, D. E.; Silva, E. D.; Lassota, P.; Allen, T. M.; Soest, R. V.; Anderson, R. J.; Boyd, M. R. J. Am. Chem. Soc. 1999, 121, 5899-5909.
2. Zampella, A.; D'Auria, M. V.; Paloma, L. G.; Casapullo, A.; Minale, L.; Debitus, C.; Henin, Y. J. Am. Chem. Soc. 1996, 118, 6202-6209.
3. Oku, N.; Gustafson, K. R.; Cartner, L. K.; Wilson, J. A.; Shigematsu, N.; Hess, S.; Pannell, L. K.; Boyd, M. R.; McMahon, J. B. J. Nat. Prod. 2004, 67, 1407-1411.
4. (a) Okamoto, N.; Hara, O.; Makino, K.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1353-1358;
5. (b) Liang, B.; Carrol, P. J.; Joullie, M. M. Org. Lett. 2000, 2, 4157-4160;
6. (c) Acevedo, C. M.; Kogut, E. F.; Lipton, M. A. Tetrahedron 2001, 57, 6353-6359;
7. (d) Makino, K.; Okamoto, N.; Hara, O.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1757-1762;
8. (e) Okamoto, N.; Hara, O.; Makino, K.; Hamada, Y. J. Org. Chem. 2002, 67, 9210-9215;
9. (f) Hansen, D. B.; Wan, X.; Carroll, P. J.; Joullie, M. M. J. Org. Chem. 2005, 70, 3120-3126;
10. (g) Makino, K.; Goto, T.; Hiroki, Y.; Hamada, Y. Angew. Chem., Int. Ed. 2004, 43, 882-884;
11. (h) Makino, K.; Hiroki, Y.; Hamada, Y. J. Am. Chem. Soc. 2005, 127, 5784-5785.
12. (a) Guerlavais, V.; Carroll, P. J.; Joullie, M. M. Tetrahedron Lett. 2002, 13, 675-680;
13. (b) Zampella, A.; Sorgente, M.; D'Auria, M. V. Tetrahedron: Asymmetry 2002, 13, 681-685;
14. (c) Zampella, A.; D'Auria, M. V. Tetrahedron: Asymmetry 2002, 13, 1237-1239;
15. (d) Chandrasekhar, S.; Ramchandar, T.; Rao, B. V. Tetrahedron: Asymmetry 2001, 12, 2315-2321;
16. (e) Thoen, J. C.; Morales-Ramos, A. I.; Lipton, M. A. Org. Lett. 2002, 4, 4455-4458;
17. (f) Kumar, A. R.; Rao, B. V. Tetrahedron Lett. 2003, 44, 5645-5647;
18. (g) Turk, J. A.; Visbal, G. S.; Lipton, M. A. J. Org. Chem. 2003, 68, 7841-7844.
19. (a) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979-2984;
20. (b) Garner, P.; Park, J. M. Org. Synth. 1992, 70, 18-28.
21. (a) McDermott, J. R.; Benoiton, N. L. Can. J. Chem. 1973, 51, 1915-1919;
22. (b) Cheung, S. T.; Benoiton, N. L. Can. J. Chem. 1977, 55, 906-910.
23. (a) Aurelio, L.; Brownlee, B. T. C.; Hughes, A. B.; Sleebs, B. E. Aust. J. Chem. 2000, 53, 425-433;
24. (b) Chruma, J. J.; Sames, D.; Polt, R. Tetrahedron Lett. 1997, 38, 5085-5086.