Synthesis of IB-01211, a cyclic peptide containing 2,4-concatenated thia- and oxazoles, via Hantzsch macrocyclization

Organic Letters

Volumn 9, Issue 5, 2007, Pages 809-811

  Hernández, Delia ^a   Vilar, Gemma ^a   Riego, Estela ^a   Cañedo, Librada M ^b   Cuevas, Carmen ^c   Albericio, Fernando ^a,d   Álvarez, Mercedes ^a,d  

^a Barcelona Science Park   (Spain)

^b Instituto Biomar SA   (Spain)

^c PHARMAMAR S A   (Spain)

^d UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE; IB 01211; IB-01211; OXAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

CYCLIZATION; MOLECULAR STRUCTURE; OXAZOLES; PEPTIDES, CYCLIC;

EID: 33947132690     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol063023c     Document Type: Article

References (29)

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3. Romero, F.; Malet, L.; Cañedo, M. L.; Cuevas, C.; Reyes, J. WO 2005/000880 A2, 2005.
4. The same structure was proposed for mechercharmycin A, isolated from a marine-derived Thermoactinomices sp., by: Kanoh, K.; Matsuo, Y.; Adachi, K.; Imagawa, H.; Nishizawa, M.; Shizuri, Y. J. Antibiot. 2005, 58, 289.
5. Cañedo, M. L.; Martínez, M.; Sánchez, J. M.; Fernández-Puentes, J. L.; Malet, L.; Pérez, J.; Romero, F.; García, L. F. 4th European Conference on Marine Natural Products, Paris, 2005, poster 54.
6. Recently, Pattenden and Deeley (Deeley, J.; Pattenden, G. Chem. Commun. 2005, 797)
7. and Takahashi et al. (Doi, T.; Yoshida, M.; Shin-ya, K.; Takahashi, T. Org. Lett. 2006, 8, 4165) have published syntheses of YM-216391 and telomestatin, respectively, which are other cyclopeptides containing concatenated azoles.
8. Telomestatin was described in a patent by Yamada, S.; Shigeno, K.; Kitagawa, K.; Okajima, S.; Asao, T. (Taiho Pharmaceutical Co. Ltd., SoseiCo. Ltd.) WO2002248153, 2002; Chem. Abstr. 2002, 137, 47050.
9. For a recent review, see: Riego, E.; Hernández, D.; Albericio, F.; Álvarez, M. Synthesis 2005, 1907.
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20. Temperature control is crucial in this step because dehydration was a severe side reaction favored by higher temperatures.
21. 3CN were assayed, but in all cases the partially oxidized system was the major product.
22. This strategy was used only for the preparation of the tetrathiazoline/thiazole of (-)-mirabazole by Akaji, K.; Kuriyama, N.; Kiso, Y. J. Org. Chem. 1996, 61, 3350,
23. and in the synthesis of tiangazole, which contains a tetrathiazoline/ oxazole system by: Wipf, P.; Venkatraman, S. Synlett 1997, 1.
24. The global yield working on a 500 mg scale was 57%. However, with 2 g of tripeptides, it decreased to 32%, which is still superior to the 28% obtained by sequential formation of the oxazole rings.
25. 1H NMR by the relative integration of the methyl ester singlets of 9 (3.92 ppm) and 10 (3.84 ppm). A sign of the formation of 10 was the upfield shift of the phenyl protons as compared to those of 9, which occurs as a result of their conjugation with the ester. For the ortho protons, the difference in chemical shift is 0.5 ppm.
26. Other reagents, such as the Burgess reagent, did not improve the results.
27. Alternatively, and to avoid the elimination side reaction, the phenyloxazole was also obtained from a route that involves reaction of the ketoamide formed by Swern oxidation, as described by: Wipf, P.; Miller, C. P. J. Org. Chem. 1993, 58, 3604. (Chemical Equation Presented)
28. Obtained by saponification of the methyl bromopyruvate dimethyl acetal with LiOH as described by: Chari, R. V. J.; Kozarich, J. W. J. Org. Chem. 1982, 47, 23.
29. 2O + 0.045% TFA, B = MeCN + 0.036% TFA, gradient = 0-100% B in 15 min) and identical shape and wavelength in the UV detector. A sample of IB01211 was kindly supplied by the fermentation department of PharmaMar.