Synthesis of natural product derivatives containing 2,4-concatenated oxazoles

European Journal of Organic Chemistry

Volumn , Issue 19, 2008, Pages 3389-3396

  Hernández, Delia ^a   Riego, Estela ^a   Albericio, Fernando ^a   Álvarez, Mercedes ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Concatenated oxazoles; Macrocyclization; Nitrogen heterocycles; Peptides

Indexed keywords

EID: 52449085116     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800111     Document Type: Article

References (23)

1. For recent reviews, see: a) V. S. C. Yeh, Tetrahedron 2004, 60, 11995-12042;
2. b) E. Riego, D. Hernández, F. Albericio, M. Álvarez, Synthesis 2005, 1907-1922;
3. c) R. A. Hughes, C. J. Moody, Angew. Chem. Int. Ed. 2007, 46, 2-27.
4. T. Ichiba, W. Y. Yoshida, P. J. Scheuer, J. Am. Chem. Soc. 1991, 113, 3173-3175.
5. A. Nagatsu, H. Kajitani, J. Sakakibara, Tetrahedron Lett. 1995, 36, 4097-4100.
6. J. A. Roesener, P. J. Scheuer, J. Am. Chem. Soc. 1986, 108, 846-847.
7. S. Matsunaga, N. Fusetani, K. Hashimoto, K. Koseki, M. Noma, J. Am. Chem. Soc. 1986, 108, 847-849.
8. P. Phuwapraisirisan, S. Matsunaga, R. W. M. van Soest, N. Fusetani, J. Nat. Prod. 2002, 65, 942-943.
9. S. Matsunaga, N. Fusetani, K. Hashimoto, K. Koseki, M. Noma, H. Noguchi, U. Sankawa, J. Org. Chem. 1989, 54, 1360-1363.
10. N. Lindquist, W. Fenical, G. D. Van Duyne, J. Clardy, J. Am. Chem. Soc. 1991, 113, 2303-2304.
11. a) K. Shin-ya, K. Wierzba, K. Matsuo, T. Ohtani, Y. Yamada, K. Furihata, Y. Hayakawa, H. Seto, J. Am. Chem. Soc. 2001, 123, 1262-1263;
12. b) M.-Y. Kim, H. Vankayalapati, K. Shin-ya, K. Wierzba, L. H. Hurley, J. Am. Chem. Soc. 2002, 124, 2098-2099.
13. A. Hayata, Y. Takebashi, K. Nagai, M. Hiramoto (Japan Kokai Tokkyo Koho), JP11180997-A, 1999 [Chem. Abstr. 1999, 131, 101307].
14. a) F. Romero, L. Malet, M. L. Cañedo, C. Cuevas, F. Reyes, WO 2005/000880 A2, 2005;
15. b) the same structure was proposed for Merchercharmycin A, which was isolated from a marine-derived Thermoactinomices sp. by K. Kanoh, Y. Matsuo, K. Adachi, H. Imagawa, M. Nishizawa, Y. Shizuri, J. Antibiot. 2005, 58, 289-292.
16. D. Hernández, G. Vilar, E. Riego, L. M. Cañedo, C. Cuevas, F. Albericio, M. Álvarez, Org. Lett. 2007, 9, 809-811.
17. D. Hernández, E. Riego, A. Francesch, C. Cuevas, F. Albericio, M. Álvarez, Tetrahedron 2007, 63, 9862-9870.
18. D-Ile or L-Ile was used for the previous studies of preparation of analogs instead of the D-Allo-Ile present in the natural product for economical reasons.
19. J. C. Muir, G. Pattenden, R. M. Thomas, Synthesis 1998, 613.
20. Peptides 16a and 16b were obtained by amide bond formation between the peptide H-D-Ile-L-Val-OMe and the free acid of 15a or 15b, respectively. Peptides 15a and 15b were obtained by amide bond formation between the free amine of 11a and 11b and the free carboxylic acid of 11a, respectively.
21. Compound 16a, which has the same structure as that of 16b but without the phenyl ring, did not undergo macrocyclization under the conditions tested for 16b.
22. Peptide 17 was obtained from the free acid of 7 and H-D-Ile-L-Val-OMe by using the general procedure described for peptide bond formation.
23. R = 7.56 min; MS: m/z = 845 [M + K], 829 [M + Na]).