Organolithium-mediated diversification of peptide thiazoles

Organic Letters

Volumn 7, Issue 2, 2005, Pages 299-301

  Deng, Shaojiang ^a   Taunton, Jack ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ESTER DERIVATIVE; ORGANOLITHIUM COMPOUND; PEPTIDE; THIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; LITHIATION; RACEMIZATION;

EID: 13444282243     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047660j     Document Type: Article

References (25)

1. For a review on biosynthesis, see: (a) Roy, R. S., Gehring, A. M.; Milne, J. C.; Belshaw, P. J.; Walsh, C. T. Nat. Prod. Rep. 1999, 16, 249. For reviews on isolation, see: (b) Jin, Z. Nat. Prod. Rep. 2003, 20, 584 and references contained therein.
2. For a review on biosynthesis, see: (a) Roy, R. S., Gehring, A. M.; Milne, J. C.; Belshaw, P. J.; Walsh, C. T. Nat. Prod. Rep. 1999, 16, 249. For reviews on isolation, see: (b) Jin, Z. Nat. Prod. Rep. 2003, 20, 584 and references contained therein.
3. Sasse, F.; Steinmetz, H.; Schupp, T.; Petersen, F.; Memmert, K.; Hofmann, H.; Heusser, C.; Brinkmann, V.; Von Matt, P.; Hofle, G.; Reichenbach, H. J. Antibiot. 2002, 55, 543.
4. (a) Rodnina, M. V.; Savelsbergh, A.; Matassova, N. B.; Katunin, V. I.; Semenkov, Y. P.; Wintermeyer, W. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 9586.
5. (b) Cameron, D. M.; Thompson, J.; March, P. E.; Dahlberg, A. E. J. Mol. Biol. 2002, 319, 27.
6. Marquez, B. L.; Watts, K. S.; Yokochi, A.; Roberts, M. A.; Verdier-Pinard, P.; Jimenez, J. I.; Hamel, E.; Scheuer, P. J.; Gerwick, W. H. J. Nat. Prod. 2002, 65, 866.
7. (a) Wipf, P.; Fritch, P. C.; Geib, S. J.; Sefler, A. M. J. Am. Chem. Soc. 1998, 120, 4105.
8. (b) Somogyi, L.; Haberhauer, G.; Rebek, J., Jr. Tetrahedron 2001, 57, 1699.
9. (c) Singh, Y.; Stoermer, M. J.; Lucke, A. J.; Glenn, M. P.; Fairlie, D. P. Org. Lett. 2002, 4, 3367.
10. For examples of peptide thiazole natural products with 5-methyl and 5-methoxymethyl substituents, see: (a) Selva, E.; Beretta, G.; Montanini, N.; Saddler, G. S.; Gastaldo, L.; Ferrari, P.; Lorenzetti, R.; Landini, P.; Ripamonti, F.; Goldstein, B. P. J. Antibiot. 1991, 44, 693. (b) Shimanaka, K.; Kinoshita, N.; Iinuma, H.; Hamada, M.; Takeuchi, T. J. Antibiot. 1994, 47, 668.
11. For examples of peptide thiazole natural products with 5-methyl and 5-methoxymethyl substituents, see: (a) Selva, E.; Beretta, G.; Montanini, N.; Saddler, G. S.; Gastaldo, L.; Ferrari, P.; Lorenzetti, R.; Landini, P.; Ripamonti, F.; Goldstein, B. P. J. Antibiot. 1991, 44, 693. (b) Shimanaka, K.; Kinoshita, N.; Iinuma, H.; Hamada, M.; Takeuchi, T. J. Antibiot. 1994, 47, 668.
12. (a) Gordon, T. D.; Singh, J.; Hansen, P. E.; Morgan, B. A. Tetrahedron Lett. 1993, 34, 1901.
13. (b) Buchanan, J. L.; Mani, U. N.; Plake, H. R.; Holt, D. A. Tetrahedron Lett. 1999, 40, 3985.
14. (c) Suzuki, T.; Nagasaki, A.; Okumura, K.; Shin, C.-G. Heterocycles 2001, 55, 835.
15. (d) Nagasaki, A.; Adachi, Y.; Yonezawa, Y.; Shin, C.-G. Heterocycles 2003, 60, 321.
16. Metzger, J. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 6, pp 235-331.
17. Tan, L. T.; Williamson, R. T.; Gerwick, W. H.; Watts, K. S.; McGough, K.; Jacobs, R. J. Org. Chem. 2000, 65, 419.
18. (a) Yokokawa, F.; Sameshima, H.; Shioiri, T. Synlett 2001, 986.
19. (b) Deng, S.; Taunton, J. J. Am. Chem. Soc. 2002, 124, 916.
20. (c) Kutsumura, N.; Sata, N. U.; Nishiyama, S. Bull. Chem. Soc. Jpn. 2002, 75, 847.
21. (d) Yokokawa, F.; Sameshima, H.; In, Y.; Minoura, K.; Ishida, T.; Shioiri, T. Tetrahedron 2002, 58, 8127.
22. Lithiated thiazole l is stable at -78°C for up to 30 min, with ∼5% self-acylation product and ∼10% other decomposition products; lithiated thiazole 2 is stable at -78°C for at least 30 min with less than 2% self-acylation product. Both decompose rapidly at -40°C.
23. Fujii, K.; Ikai, Y.; Oka, H.; Suzuki, M.; Harada, K. Anal. Chem. 1997, 69, 5146.
24. Brummond, K. M.; Gesenkerg, K. D. Tetrahedron Lett. 1999, 40, 2231.
25. Abarbri, M.; Thibonnet, J.; Bérillon, L.; Dehmel, F.; Rottländer, M.; Knochel, P. J. Org. Chem. 2000, 65, 4618.