Synthesis of peptides containing 2,3-methanoaspartic acid

Tetrahedron Letters

Volumn 38, Issue 23, 1997, Pages 4065-4068

  Godier Marc, Emmanuelle ^a   Aitken, David J ^a   Husson, Henri Philippe ^a  

^a FACULTÉ DES SCIENCES PHARMACEUTIQUES ET BIOLOGIQUES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; ASPARTIC ACID DERIVATIVE; DIPEPTIDE DERIVATIVE; TRIPEPTIDE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; OXIDATION; PEPTIDE SYNTHESIS;

EID: 0030944661     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00800-9     Document Type: Article

References (27)

1. (a) Salaün, J.; Baird, M. S. Curr. Med. Chem., 1995, 2, 511-542
2. (b) Burgess, K.; Ho, K.-K.; Moye-Sherman, D. Synlett, 1994, 575-583
3. (c) Kodama, H.; Shimohigashi, Y. Yuki Goesi Kagaku Kyokaishi, 1994, 52, 180-191 (Chem. Abstr., 1994, 720, 299214r)
4. (c) Kodama, H.; Shimohigashi, Y. Yuki Goesi Kagaku Kyokaishi, 1994, 52, 180-191 (Chem. Abstr., 1994, 720, 299214r)
5. (d) Alami, A.; Calmes, M.; Daunis, J.; Jacquier, R. Bull. Soc. Chim. Fr., 1993, 130, 5-24
6. (e) Stammer, C. H. Tetrahedron, 1990, 46, 2231-2254.
7. Taylor, E. C.; Hu, B. Synth. Commun., 1996, 26, 1041-1049.
8. For other examples of this phenomenon, see: (a) Kaufman, M. D.; Grieco, P. A. J. Org. Chem., 1994, 59, 7197-7198
9. (b) Paulini, K.; Reißig, H.-U. Leibigs Ann. Chem., 1991, 455-461
10. (c) Cannon, J. G.; Garst, J. E. J. Org. Chem., 1975, 40, 182-184
11. (d) Gebhardt-Schmitz, A.; Mennicken, H.; Schmitz, F.; Lipp, P.; Lipp, M. Tetrahedron Lett., 1962, 227-228. For a vinylogous example, see: Bruncko, M.; Crich, D. J. Org. Chem., 1994, 59, 4239-4249.
12. (d) Gebhardt-Schmitz, A.; Mennicken, H.; Schmitz, F.; Lipp, P.; Lipp, M. Tetrahedron Lett., 1962, 227-228. For a vinylogous example, see: Bruncko, M.; Crich, D. J. Org. Chem., 1994, 59, 4239-4249.
13. Kraus, G. A.; Kim, H.; Thomas, P. J.; Metzler, D. E.; Metzler, C. M.; Taylor, J. E. Synth. Commun., 1990, 20, 2667-2673.
14. Wick, L.; Tamm, C.; Boller, T. Helv. Chim. Acta, 1995, 78, 403-410.
15. Jiménez, J.; Rife, J.; Ortuño, R. M. Tetrahedron: Asymmetry, 1996, 7, 537-558.
16. Horikawa, H.; Nishitani, T.; Iwasaki, T.; Inoue, I. Tetrahedron Lett., 1983, 24, 2193-2194.
17. (a) Aitken, D. J.; Royer, J.; Husson, H.-P. J. Org. Chem., 1990, 55, 2814-2820
18. (b) Guillaume, G.; Aitken, D. J.; Husson, H.-P. Synlett, 1991, 747-749.
19. (a) Es-Sayed, M.; Gratkowski, C.; Krass, N.; Meyers, A. I.; de Meijere, A. Synlett, 1993, 962-964
20. (b) Koskinen, A.M.P.; Muños, L. J. Org. Chem., 1993, 58, 879-886
21. (c) Burgess, K.; Ho, K.K. J. Org. Chem., 1992, 57, 5931-5936
22. (d) Fliche, C.; Braun, J.; Le Goffic, F. Synth. Commun., 1991, 21, 1429-1432
23. (e) Pirrung, M.C.; Dunlap, S.E.; Trinks, U.P. Helv. Chim Acta, 1989, 72, 1301-1310
24. (f) Bland, J.; Shah, A.; Bortolussi, A.; Stammer, C.H. J. Org. Chem., 1988, 53, 992-995.
25. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem., 1981, 46, 3936-3938.
26. All new compounds presented herein showed satisfactory spectral and/or analytical data. Peptides 4-7, 11-15 and 19 were obtained as 1:1 diastereomeric mixtures and caracterized as such. No epimerization was observed in the described procedures.
27. 4), Jones' reagent gave 15 from 7 in 45% yield. Others were less efficient or failed completely.