Hexafluoroacetone as Protecting and Activating Reagent: An Efficient Strategy for Activation of Pyroglutamic Acid and Homologues

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20130710112544

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2009-03-04T23:45:09Z

HETEROCYCLES HETEROCYCLES 0385-5414 HTCYAM 2003 61 1 Hexafluoroacetone as Protecting and Activating Reagent: An Efficient Strategy for Activation of Pyroglutamic Acid and Homologues Klaus Burger Ksenia Pumpor Christoph Böttcher Susanna Fehn 2003 259 COM-03-S34 10.3987/COM-03-S34 20130710112544 https://triggered.stanford.clockss.org/ServeContent?doi=10.3987%2Fcom-03-s34 https://triggered.edinburgh.clockss.org/ServeContent?doi=10.3987%2Fcom-03-s34 10.1021/jm00137a027 1. A. Barco, S. Benetti, G. P. Pollini, P. G. Baraldi, and M. Guaneri, J. Med. Chem., 1981, 24, 625. 10.1016/S0968-0896(98)80015-1 2. G. K. Kar, B. C. Roy, S. D. Adhikari, J. K. Ray, and N. K. Brahma, Bioorg. Med. Chem., 1998, 6, 2397. 3. G. L. Olson, H. C. Cheung, M. E. Voss, D. E. Hill, M. Kahn, V. S. Madison, C. M. Cook, and J. Sepinwall, Eds., Proceeding of the Biotech. USA, 89 Meeting, San Francisco, October, 1989. 10.1002/1521-3765(20020603)8:11<2516::AID-CHEM2516>3.0.CO;2-K (a) F. Bernardi, M. Garavelli, M. Scatizzi, C. Tomasini, V. Trigari, M. Crisma, F. Formaggio, C. Peggion, and C. Toniolo, Chem. Eur. J., 2002, 8, 2516; 10.1021/jo026233l (b) G. Luppi, D. Lanci, V. Trigari, M. Garavelli, A. Garelli, and C. Tomasini, J. Org. Chem., 2003, 68, 1982. 10.1146/annurev.pa.21.040181.001121 (a) J. C. Watkins and R. H. Evans, Ann. Rev. Pharmacol. Toxicol., 1981, 21, 165; 10.1016/0306-4522(83)90263-4 (b) G. E. Fagg and A. C. Forster, Neuroscience, 1983, 9, 701. 10.1021/cr9300348 6. F. J. Sardina and H. Rapoport, Chem. Rev., 1996, 96, 1825. 10.1016/S0099-9598(08)60134-0 7. M. Wink, The Alkaloids, 1993, 43, 1. 10.1016/0040-4020(96)00732-6 8. H. McAlonan, J. P. Murphy, P. J. Stevenson, and A. B. Treacy, Tetrahedron, 1996, 52, 12521. 10.1021/jm9600196 9. P. A. Reddy, B. C. H. Hsiang, N. T. Latifi, M. W. Hill, K. E. Woodvard, S. M. Rothman, J. A. Ferrendelli, and D. F. Covey, J. Med. Chem., 1996, 39, 1898. 10.1016/S0223-5234(98)80045-7 10. M. Bouygues, M. Medou, J.-C. Chermam, M. Camplo, and J.-L. Krauss, Eur. J. Med. Chem., 1998, 33, 445. 10.1055/s-1993-22438 (a) Z. Y. Wei and E. E. Knauss, Synlett., 1993, 295; (b) M. Banzinger, J. F. McGarrity, and T. Meul, J. Org. Chem., 1993, 58, 4011. 10.1016/S0957-4166(99)00018-X (a) P. Camps, F. Perez, N. Soldevilla, and M. Borrego, Tetrahedron Asymmetry, 1999, 10, 493; 10.1016/S0957-4166(98)00194-3 (b) P. Camps, F. Perez, and N. Soldevilla, Tetrahedron Asymmetry, 1998, 9, 2065. 10.1002/ange.200390174 13. D. Seebach, L. Schaeffer, M. Brenner, and D. Hoyer, Angew. Chem., Int. Ed., 2003, 115, 800. 10.1002/cber.19660990507 14. F. Weygand, K. Burger, and K. Engelhardt, Chem. Ber., 1966, 99, 1461. (a) M. Rudolph, PhD Thesis, Technical University Munich, 1991; (b) S. Fehn, PhD Thesis, Technical University Munich, 1995. 10.1016/0040-4020(96)00942-8 (a) A. S. Golubev, N. Sewald, and K. Burger, Tetrahedron, 1996, 52, 14757; 10.1016/S0040-4039(00)73803-2 (b) A. S. Golubev, N. Sewald, and K. Burger, Tetrahedron Lett., 1993, 34, 5879. 10.1016/S0040-4039(99)02208-X 17. J. M. Alvarez-Gutierrez, A. Nefzi, and R. A. Houghten, Tetrahedron Lett., 2000, 41, 851. 18. H.-P. Krimmer, K. Drauz, and H. Klenk, Chem.-Ztg., 1990, 114, 117. 19. Dictionary of Organic Compounds, 6th ed.; Chapman and Hall, London, 1996. 10.1021/bi00831a015 20. S. Takahashi and L. A. Cohen, Biochem., 1969, 8, 864.