Enantioselective syntheses of bicyclo[3.1.0]hexane carboxylic acid derivatives by intramolecular cyclopropanation

Tetrahedron Letters

Volumn 45, Issue 39, 2004, Pages 7261-7264

  Yoshikawa, Naoki ^a   Tan, Lushi ^a   Yasuda, Nobuyoshi ^a   Volante, Ralph P ^a   Tillyer, Richard D ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Claisen rearrangement; Cyclopropanation; Fluorinated cyclopropane; mGluR agonist

Indexed keywords

BICYCLO COMPOUND; CARBOXYLIC ACID DERIVATIVE; HEXANE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; MOLECULAR INTERACTION; REACTION ANALYSIS;

EID: 4444373880     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.027     Document Type: Article

References (26)

1. D.T. Monaghan, R.J. Bridges, and C.W. Cotman Annu. Rev. Pharmacol. Toxicol. 29 1989 365 402
2. S. Nakanishi Science 258 1992 597 603
3. S. Nakanishi, and M. Masu Annu. Rev. Biophys. Biomol. Struct. 23 1994 319 348
4. M. Hollmann, and S. Heinemann Annu. Rev. Neurosci. 17 1994 31 108
5. A.A. Schoepp, D.A. Jane, and J.A. Monn Neuropharmacology 38 1999 1431 1476
6. L.E. Chavez-Noriega, H. Schaffhauser, and U.C. Campbell Curr. Drug Targets 1 2002 261 281
7. J.-P. Pin, and F. Acher Curr. Drug Targets 1 2002 297 317
8. J.A. Monn, M.J. Valli, S.M. Massey, R.A. Wright, C.R. Salhoff, B.G. Johnson, T. Howe, C.A. Alt, G.A. Rhodes, R.L. Robey, K.R. Griffey, J.P. Tizzano, M.J. Kallman, D.R. Helton, and D.D. Schoepp J. Med. Chem. 40 1997 528 537
9. B. Moghaddam, and B.W. Adams Science 281 1998 1349 1352
10. L.E. Chavez-Noriega, H. Schaffhauser, and U.C. Campbell Curr. Drug Targets 1 2002 261 281
11. J.A. Monn, M.J. Valli, S.M. Massey, M.M. Hansen, T.J. Kress, J.P. Wepsiec, A.R. Harkness, J.L. Grutsch Jr., R.A. Wright, B.G. Johnson, S.L. Andis, A. Kingston, R. Tomlinson, R. Lewis, K.R. Griffey, J.P. Tizzano, and D.D. Schoepp J. Med. Chem. 42 1999 1027 1040 See also Ref. 8
12. A. Nakazato, T. Kumagai, K. Sakagami, R. Yoshikawa, Y. Suzuki, S. Chaki, H. Ito, T. Taguchi, S. Nakanishi, and S. Okuyama J. Med. Chem. 43 2000 4893 4909
13. C. Domínguez, J. Ezquerra, L. Prieto, M. Espada, and C. Pedregal Tetrahedron: Asymmetry 8 1997 511514
14. C. Domínguez, J. Ezquerra, S.R. Baker, S. Borrelly, L. Prieto, M. Espada, and C. Pedregal Tetrahedron Lett. 39 1998 9305 9308
15. E.D. Moher Tetrahedron Lett. 37 1996 8637 8640
16. Y. Ohfune, T. Demura, S. Iwama, H. Matsuda, K. Namba, K. Shimamoto, and T. Shinada Tetrahedron Lett. 44 2003 5431
17. A. Wong, C.J. Welch, J.T. Kuethe, E. Vazquez, M. Shaimi, D. Henderson, I.W. Davies, and D.L. Hughes Org. Biomol. Chem. 2 2004 168 174
18. Manuscript submitted
19. W.R. Dolbier Jr., and M.A. Battiste Chem. Rev. 103 2003 1071 1098
20. T. Taguchi, H. Sasaki, A. Shibuya, and T. Morikawa Tetrahedron Lett. 35 1994 913 916
21. A. Saito, H. Ito, and T. Taguchi Tetrahedron 57 2001 7487 7493
22. E. Differding, and H. Ofner Synlett 1991 187 189
23. The cyclization was also examined using O-PMB or O-trityl compound instead of O-TBS compound 12 to see the effects of the protecting group on the conformation depicted in Figure 2. The desired bicyclic compound, however, was not obtained
24. D.M. Hodgson, and A.R. Gibbs Synlett 1997 657 658
25. K. Kondo, M. Matsumoto, and F. Mori Angew. Chem., Int. Ed. Engl. 14 1975 103
26. Cyclization using the other isomer with respect to the carbon-fluorine bond was not examined