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Volumn 9, Issue 8, 2007, Pages 1593-1596

Exceptional stereoselectivity in the synthesis of 1,3,4-trisubstituted 4-carboxy β-lactam derivatives from amino acids

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; BETA LACTAM; DIPEPTIDE;

EID: 34247483127     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070533d     Document Type: Article
Times cited : (31)

References (36)
  • 1
    • 3042709445 scopus 로고    scopus 로고
    • For recent reviews on the biological activity of β-lactams, see: a
    • For recent reviews on the biological activity of β-lactams, see: (a) Singh, G. S. Mini-Rev. Med. Chem. 2004, 4, 69.
    • (2004) Mini-Rev. Med. Chem , vol.4 , pp. 69
    • Singh, G.S.1
  • 29
    • 34247541681 scopus 로고    scopus 로고
    • R: 5b = 9.75 min.
    • R: 5b = 9.75 min.
  • 32
    • 34247537977 scopus 로고    scopus 로고
    • Full details of the coupling agents and bases used for the optimization of the synthesis of 9a are indicated in the Supporting Information.
    • Full details of the coupling agents and bases used for the optimization of the synthesis of 9a are indicated in the Supporting Information.
  • 33
    • 34247495572 scopus 로고    scopus 로고
    • Diastereoisomeric excess values: 9a (96%), 9b (92%), 10a (83%), 10b (81%), 11a (98%), and 11b (98%). Measured by HPLC.
    • Diastereoisomeric excess values: 9a (96%), 9b (92%), 10a (83%), 10b (81%), 11a (98%), and 11b (98%). Measured by HPLC.
  • 34
    • 0025801244 scopus 로고    scopus 로고
    • For configurational assignments in dipeptide derivatives composed by one aliphatic and one aromatic amino acid, see: (a) González-Muñiz, R:; Cornille, F, Bergeron, F, Ficheux, D, Pothier, J, Durieux, C, Roques, B. P. Int. J. Pept. Protein Res. 1991, 37, 331
    • For configurational assignments in dipeptide derivatives composed by one aliphatic and one aromatic amino acid, see: (a) González-Muñiz, R:; Cornille, F.; Bergeron, F.; Ficheux, D.; Pothier, J.; Durieux, C.; Roques, B. P. Int. J. Pept. Protein Res. 1991, 37, 331.
  • 36
    • 0037204722 scopus 로고    scopus 로고
    • The validity of these rules has unequivocally been demonstrated for a related dipeptide derivative composed by a Phe-derived β-lactam, without the 3-methyl substituent, and L-Ala-OMe: Gerona-Navarro, G, García-López, M. T, González-Muñiz, R. J. Org. Chem. 2002, 67, 3953
    • The validity of these rules has unequivocally been demonstrated for a related dipeptide derivative composed by a Phe-derived β-lactam, without the 3-methyl substituent, and L-Ala-OMe: Gerona-Navarro, G.; García-López, M. T.; González-Muñiz, R. J. Org. Chem. 2002, 67, 3953.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.