Stereocontrolled synthesis of a potent agonist of group II metabotropic glutamate receptors, (+)-LY354740, and its related derivatives

Tetrahedron Letters

Volumn 44, Issue 29, 2003, Pages 5431-5434

  Ohfune, Yasufumi ^a   Demura, Takashi ^a   Iwama, Seiji ^a   Matsuda, Hiromi ^a   Namba, Kosuke ^a   Shimamoto, Keiko ^b   Shinada, Tetsuro ^a  

^a Osaka Prefecture University   (Japan)

^b SUNTORY INSTITUTE FOR BIOORGANIC RESEARCH   (Japan)

Author keywords

DCG IV; Dehydration; Glutamate analog; L CCG III; LY354740; MGluRs agonist; Transport inhibitor; 2+3 dipolar cycloaddition:cyclopropanation:epimerization; diazo acetamide

Indexed keywords

1 AMINO 2 HYDROXYCYCLOPENTANE; ACETAMIDE DERIVATIVE; ALPHA DIAZOACETAMIDE; CYCLOHEXANECARBOXYLIC ACID DERIVATIVE; CYCLOPENTANE DERIVATIVE; EGLUMETAD; METABOTROPIC RECEPTOR AGONIST; UNCLASSIFIED DRUG;

ARTICLE; CYCLOPROPANATION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0037863192     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01316-9     Document Type: Article

References (41)

1. Collingridge G.L., Lester R.A. Pharmacol. Rev. 1989, 40, 143-210
2. Parthasarathy, H. S., Ed.; Neurological disorders. Nature 1999, 399 (Suppl.), A1-A47.
3. Nakanishi S. Science. 258:1992;597-603.
4. Ishida M., Saitoh T., Shimamoto K., Ohfune Y., Shinozaki H. Br. J. Pharmacol. 109:1993;1169-1177.
5. Hayashi Y., Moriyama A., Takahashi T., Ohishi H., Ogawa-Meguro R., Shigemoto R., Mizuno N., Nakanishi S. Nature. 366:1993;687-688.
6. Conn P.J., Pin J.-P. Annu. Rev. Pharmacol. Toxicol. 37:1997;205-237. and references cited therein.
7. Ohfune Y., Shimamoto K., Ishida M., Shinozaki H. Bioorg. Med. Chem. Lett. 3:1993;15-18.
8. Shimamoto K., Ohfune Y. J. Med. Chem. 39:1996;407-423.
9. Bertrand H.-O., Bessis A.-S., Pin J.-P., Acher F.C. J. Med. Chem. 45:2002;3171-3183.
10. Monn J.A., Valli M.J., Massey S.M., Wright R.A., Salhoff C.R., Johnson B.G., Howe T., Alt C.A., Rhodes G.A., Robey R.L., Griffey K.R., Tizzano J.P., Kallman M.J., Helton D.R., Schoepp D.D. J. Med. Chem. 40:1997;528-537.
11. Both DCG-IV and LY354740 and their radio active derivatives are commercially available from Tocris Co. Ltd., UK.
12. Recently, a potent and selective agonist of mGluR2 has been developed, see: Collado I., Pedregal C., Mazon A., Espinosa J.F., Blanco-Urgoiti J., Schoepp D.D., Wright R.A., Johnson B.G., Kingston A. J. Med. Chem. 45:2002;3619-3629.
13. Dominguez C., Ezquerra J., Prieto L., Espada M., Pedregal C. Tetrahedron: Asymmetry. 8:1997;511-514.
14. Bridges R.J., Kavanaugh M.P., Chamberlin A.R. Curr. Pharm. Des. 5:1999;363.
15. Moon S.-H., Ohfune Y. J. Am. Chem. Soc. 116:1994;7405-7406.
16. Horikawa M., Nakajima T., Ohfune Y. Synlett. 1997;253-254.
17. Ohfune Y., Nanba K., Takada I., Kan T., Horikawa M., Nakajima T. Chirality. 9:1997;459-462.
18. Ohfune Y., Horikawa M. J. Syn. Org. Chem. Jpn. 55:1997;982-993.
19. Namba K., Shinada T., Teramoto T., Ohfune Y. J. Am. Chem. Soc. 122:2000;10708-10709.
20. Iwama S., Gao W.-G., Shinada T., Ohfune Y. Synlett. 2000;1631-1633.
21. Kawasaki M., Namba K., Tsujishima H., Shinada T., Ohfune Y. Tetrahedron Lett. 2003, 44, 1234-1238;
22. Ohfune, Y.; Shinada, T. Bull. Chem. Soc. Jpn., in press.
23. Honda T., Koizumi T., Komatsuzaki Y., Yamashita R., Kanai K., Nagase H. Tetrahedron: Asymmetry. 10:1999;2703-2712.
24. CN′ reaction of the initially formed β-TfO group with the internal carbamate group occurred.
25. In fact, hydrogenation of N-benzyl lactam corresponding to 11 gave an N-benzyl bicyclic lactam where the cyclopropyl group was cleaved.
26. Doyle M.P., Shanklin M.S., Pho H.Q. Tetrahedron Lett. 29:1988;2619-2642.
27. Padwa A., Ku H. J. Org. Chem. 45:1980;3756-3766.
28. Rife J., Ortuno R.M. J. Org. Chem. 64:1999;8959-8961.
29. Yoshimura J., Yamaura M., Suzuki T., Hashimoto H. Chem. Lett. 1983;1001-1002.
30. Smith A.B. III, Friestad G.K., Barbosa J., Bertounesque E., Daun J.J.-W., Hull K.G., Iwashima M., Qiu Y., Spoors G., Salvatore B.A. J. Am. Chem. Soc. 121:1999;10478-10486.
31. Borch R.F., Bernstein M.D., Durst H.D. J. Am. Chem. Soc. 93:1971;2897-2904.
32. Ohfune Y., Tomita M., Nomoto K. J. Am. Chem. Soc. 103:1981;2409-2410.
33. Carpino L.A. J. Am. Chem. Soc. 115:1993;4397-4398.
34. Doyle M.P., Mckervey M.A., Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides. 1998;41 John Wiley & Sons.
35. Ouihia A., Rene L., Guilhem J., Pascard C., Badet B. J. Org. Chem. 58:1993;1641-1642.
36. Treatment of 10a or 10b in benzene at reflux for 4 h resulted in complete recovery of the starting material, respectively.
37. Evans D.A., Britton T.C., Ellman J.A. Tetrahedron Lett. 28:1987;6141-6144.
38. + 184.0610, found, 184.0591.
39. The same treatment using an N-Boc α-amino acid ester (Boc-L-Phe methyl ester) did not give any ester-hydrolyzed product at all.
40. + 200.0923, found 200.0899.
41. Calculations (MOPAC: AM1) suggested that the γ-ester group of the bicyclo[4.1.0] system 22 locates at a more proximal position to the amino group (distance between the carboxyl carbon and the nitrogen is 2.64 Å[O1]) than that of the bicyclo[3.1.0] system 15 (2.88 Å).