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Volumn 5, Issue 21, 2003, Pages 3791-3794

Chemoselective Nucleophilic Attack on N-Acyl Derivatives of (S)-Ethyl 4,4-Dimethyl Pyroglutamate (DMPG)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; AMIDE; ESTER DERIVATIVE; ETHYL 4,4 DIMETHYLPYROGLUTAMATE; GLUTAMIC ACID DERIVATIVE; HYDROXYL GROUP; KETONE DERIVATIVE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0242712889     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034847m     Document Type: Article
Times cited : (10)

References (32)
  • 1
    • 0037605171 scopus 로고    scopus 로고
    • For reviews see: (a) Nájera, C.; Yus, M. Tetrahedron: Asymmetry 1999, 10, 2245-2303. (b) Coppola, G.; Schuster, H. F. In Asymmetric Synthesis. Construction of Chiral Molecules Using Amino Acids; John Wiley: New York, 1987.
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 2245-2303
    • Nájera, C.1    Yus, M.2
  • 3
    • 0033953747 scopus 로고    scopus 로고
    • For recent articles see: (a) Turner, S. C.; Zhai, H.; Rapoport, H. J. Org. Chem. 2000, 65, 861. (b) Cossy, J.; Tresnard, L.; Gomez Pardo, D. Synlett 2000, 3, 409. (c) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (d) Oliveira, D. J.; Coelho, F. Tetrahedron Lett. 2001, 42, 6793.
    • (2000) J. Org. Chem. , vol.65 , pp. 861
    • Turner, S.C.1    Zhai, H.2    Rapoport, H.3
  • 4
    • 0034050784 scopus 로고    scopus 로고
    • For recent articles see: (a) Turner, S. C.; Zhai, H.; Rapoport, H. J. Org. Chem. 2000, 65, 861. (b) Cossy, J.; Tresnard, L.; Gomez Pardo, D. Synlett 2000, 3, 409. (c) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (d) Oliveira, D. J.; Coelho, F. Tetrahedron Lett. 2001, 42, 6793.
    • (2000) Synlett , vol.3 , pp. 409
    • Cossy, J.1    Tresnard, L.2    Gomez Pardo, D.3
  • 5
    • 0035939499 scopus 로고    scopus 로고
    • For recent articles see: (a) Turner, S. C.; Zhai, H.; Rapoport, H. J. Org. Chem. 2000, 65, 861. (b) Cossy, J.; Tresnard, L.; Gomez Pardo, D. Synlett 2000, 3, 409. (c) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (d) Oliveira, D. J.; Coelho, F. Tetrahedron Lett. 2001, 42, 6793.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 4943
    • Zhang, X.1    Jiang, W.2    Schmitt, A.C.3
  • 6
    • 0035944227 scopus 로고    scopus 로고
    • For recent articles see: (a) Turner, S. C.; Zhai, H.; Rapoport, H. J. Org. Chem. 2000, 65, 861. (b) Cossy, J.; Tresnard, L.; Gomez Pardo, D. Synlett 2000, 3, 409. (c) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (d) Oliveira, D. J.; Coelho, F. Tetrahedron Lett. 2001, 42, 6793.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 6793
    • Oliveira, D.J.1    Coelho, F.2
  • 12
    • 0242427889 scopus 로고    scopus 로고
    • note
    • Compounds 6 were obtained following the general procedure previously reported for 5 (ref 5) and 6a (ref 6). Yields: 6b (73%); 6c (55%); 6d (28%); 6e (45%); 6f (70%).
  • 15
    • 0242679856 scopus 로고    scopus 로고
    • note
    • 2. The organic phase was washed with HCl (morpholine) or NaCl (alkoxydes), the solvent was evaporated, and the residue was chomatographed on silica gel with hexane/EtOAc as eluent (1:1 allowed isolation of amides and 7:3 of esters). Pyroglutamate 3 was recovered with a 3:7 mixture of solvents.
  • 19
    • 0242596087 scopus 로고    scopus 로고
    • note
    • 2. The residue obtained after evaporation of the solvent was chomatographed on silica gel with hexane/EtOAc as eluent (9:1) for isolation of ketones. Auxilar 3 was recovered as indicated in ref 10.
  • 29
    • 0031679829 scopus 로고    scopus 로고
    • Although lactones 10 are described as stable compounds (Romo, D.; Harrison, P. H. M.; Jenkins, S. I.; Riddoch, R. W.; Park, K.; Yang, H. W.; Zhao, C.; Eright, G. D. Bioorg. Med. Chem. 1998, 6, 1255) they seem to be prone to hydrolysis under these reaction conditions. Thus the reaction of 9c carried out in a NMR tube generates the corresponding hydroxy acid 11c in the reaction medium as we proved by following by NMR this conversion (see Supporting Information) discarding its formation in the workup.
    • (1998) Bioorg. Med. Chem. , vol.6 , pp. 1255
    • Romo, D.1    Harrison, P.H.M.2    Jenkins, S.I.3    Riddoch, R.W.4    Park, K.5    Yang, H.W.6    Zhao, C.7    Eright, G.D.8
  • 30
    • 0242596086 scopus 로고    scopus 로고
    • note
    • 2).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.