3936
K. Furuta et al. / Tetrahedron Letters 45 (2004) 3933–3936
Shibata, T.; Ishida, M.; Shinozaki, H. Neuroscience 1995,
68, 585–591.
Acknowledgements
6. (a) Olney, J. W.; Rhee, V.; Ho, O. L. Brain Res. 1974, 77,
507–512; (b) Coyle, J. T.; Schwarcz, R. Nature 1976, 263,
244–246; (c) McGeer, E. G.; McGeer, P. L. Nature 1976,
263, 517–519.
This work was supported in part by a Grant-in-Aid for
Creative Scientific Research ‘In vivo Molecular Science
for Discovery of New Biofunctions and Pharmaceutical
Drugs’ no. 13NP0401, from the Ministry of Education,
Culture, Sports, Science and Technology, Japan.
G.X.W. thanks the JSPS Postdoctoral Fellowship for
Foreign Researchers.
7. (a) Hashimoto, K.; Horikawa, M.; Shirahama, H. Tetra-
hedron Lett. 1990, 31, 7047–7050; (b) Hashimoto, K.;
Shirahama, H. Tetrahedron Lett. 1991, 32, 2625–2628; (c)
Ishida, M.; Shinozaki, H. Br. J. Pharmacol. 1991, 104,
873–878; For other syntheses of acromelic acid and
analogs, see: (d) Baldwin, J. E.; Fryer, A. M.; Pritchard,
G. J.; Spyvee, M. R.; Whitehead, R. C.; Wood, M. E.
Tetrahedron 1998, 54, 7465–7484; (e) Klotz, P.; Mann, A.
Tetrahedron Lett. 2003, 44, 1927–1930, and references
cited therein.
8. (a) Baldwin, J. E.; Pritchard, G. J.; Williamson, D. S.
Bioorg. Med. Chem. Lett. 2000, 10, 1927–1929; (b)
Baldwin, J. E.; Pritchard, G. J.; Williamson, D. S.
Tetrahedron 2001, 57, 7991–7997.
9. Tonnesen, G. L.; Hanson, R. N.; Seitz, D. E. Int. J. Appl.
Radiat. Isot. 1981, 32, 171–173.
References and notes
1. (a) Konno, K.; Shirahama, H.; Matsumoto, T. Tetrahe-
dron Lett. 1983, 24, 939–942; (b) Konno, K.; Hashimoto,
K.; Ohfune, Y.; Shirahama, H.; Matsumoto, T. J. Am.
Chem. Soc. 1988, 110, 4807–4815.
2. For reviews, see: (a) Shinozaki, H. In Kainic Acid as a Tool
in Neurobiology; McGeer, E. G., Olney, J. W., McGeer, P.
L., Eds.; Raven: New York, 1978; pp 17–35;
(b) Hashimoto, K.; Shirahama, H. Trends Org. Chem.
1991, 2, 1–32; (c) Parsons, A. F. Tetrahedron 1996, 52,
4149–4174; (d) Bleakman, D.; Lodge, D. Neuropharma-
cology 1998, 37, 1187–1204.
10. Azizian, H.; Eaborn, C.; Pidcock, A. J. Organomet. Chem.
1981, 215, 49–58.
11. Baldwin, J. E.; Bamford, S. J.; Fryer, A. M.; Rudolph,
M. P. W.; Wood, M. E. Tetrahedron 1997, 53, 5233–5254.
12. The oxidation of protected N-benzoyl-4-hydroxyproline
methyl ester was conducted with TEMPO (catalytic) and
trichloroisocyanuric acid (2 equiv) instead of the use of
RuCl3 and NaIO4 described in the literature, affording the
keto derivative in an improved yield (92% vs 85%) with a
simplified workup procedure..
13. Baldwin, J. E.; Fryer, A. M.; Pritchard, G. J. J. Org.
Chem. 2001, 66, 2597–2601.
14. Minami, T.; Matsumura, S.; Okuda-Ashitaka, E.; Shi-
mamoto, K.; Sakimura, K.; Mishina, M.; Mori, H.; Ito, S.
Brain Res. 2001, 895, 178–185.
15. Minami, T.; Matsumura, S.; Nishizawa, M.; Sasaguri, Y.;
Hamanaka, N.; Ito, S. in press.
16. Biological assays, such as the measurements of electro-
physiological responses and intracellular Ca2þ increase in
neurons, are currently underway and detailed descriptions
will be reported separately.
3. (a) Tsai, C.; Schneider, J. A.; Lehmann J. Neurosci. Lett.
1988, 92, 298–302; (b) Hashimoto, K.; Ohfune, Y.;
Shirahama, H. Tetrahedron Lett. 1995, 36, 6235–6238;
(c) Cantrell, B. E.; Zimmerman, D. M.; Monn, J. A.;
Kamboj, R. K.; Hoo, K. H.; Tizzano, J. P.; Pullar, I. A.;
Farrell, L. N.; Bleakman, D. J. Med. Chem. 1996, 39,
3617–3624; (d) Hollmann, M.; Heinemann, S. Annu. Rev.
Neurosci. 1994, 17, 31–108; (e) Chevliakov, M. V.;
Montgomery, J. J. Am. Chem. Soc. 1999, 121, 11139–
11143.
4. For recent reviews, see: (a) Conn, P. J.; Pin, J. P. Annu.
Rev. Pharmacol. Toxicol. 1997, 37, 205–237; (b) Moloney,
M. G. Nat. Prod. Rep. 1998, 15, 205–219; (c) Dingledine,
R.; Borges, K.; Bowie, D.; Traynelis, S. F. Pharmacol.
Rev. 1999, 51, 7–61; (d) Brauner-Osborne, H.; Egebjerg, J.;
Nielsen, E. O.; Madsen, U.; Krogsgaard-Larsen, P.
J. Med. Chem. 2000, 43, 2609–2645; (e) Schoepp, D. D.
J. Pharmacol. Exp. Ther. 2001, 299, 12–20.
5. (a) Shinozaki, H.; Ishida, M.; Gotoh, Y.; Kwak, S. Brain
Res. 1989, 503, 330–333; (b) Kwak, S.; Aizawa, H.; Ishida,
M.; Shinozaki, H. Life Sci. 1991, 49, PL91–96; (c) Tsuji,
K.; Nakamura, Y.; Ogata, T.; Mitani, A.; Kataoka, K.;
17. The compound can be handled for routine purpose of
biochemical experiments without special care under lab-
oratory conditions, and kept for months unchanged in the
refrigerator unless exposed to UV light.