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Volumn 9, Issue 1, 2007, Pages 101-104

Synthesis of β-lactam scaffolds for ditopic peptidomimetics

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE; AZIRIDINE DERIVATIVE; BETA LACTAM; BIOMIMETIC MATERIAL; PEPTIDE;

EID: 33846449122     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0626241     Document Type: Article
Times cited : (52)

References (40)
  • 3
    • 0035959447 scopus 로고    scopus 로고
    • For reviews, see: a
    • For reviews, see: (a) Souers, A. J.; Ellman, J. A. Tetrahedron 2001, 57, 7431-7448.
    • (2001) Tetrahedron , vol.57 , pp. 7431-7448
    • Souers, A.J.1    Ellman, J.A.2
  • 5
    • 10044292363 scopus 로고    scopus 로고
    • Synthesis of Peptides Incorporating β-Turn Inducers and Mimetics
    • Goodman, M, Felix, A, Moroder, L, Toniolo, C, Eds, Thieme: Stuttgart, New York, and references therein
    • (c) Kahn, M.; Eguchi, M. Synthesis of Peptides Incorporating β-Turn Inducers and Mimetics. In Houben-Weyl, Methods of Organic Chemistry; Goodman, M., Felix, A., Moroder, L., Toniolo, C., Eds.; Thieme: Stuttgart, New York, 2003; Vol. E22c, pp 695-740 and references therein.
    • (2003) Houben-Weyl, Methods of Organic Chemistry , vol.E22c , pp. 695-740
    • Kahn, M.1    Eguchi, M.2
  • 6
    • 0003461218 scopus 로고    scopus 로고
    • Lehn, J.-M, Atwood, J. L, Davies, J. E. D, MacNicol, D. D, Vögtle, F, Eds, Pergamon: Oxford
    • Comprehensive Supramolecular Chemistry; Lehn, J.-M., Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon: Oxford, 1996.
    • (1996) Comprehensive Supramolecular Chemistry
  • 11
    • 0034751733 scopus 로고    scopus 로고
    • 1 = H): (a) Turner, J. J.; Sikkema, F. D.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Synlett 2001, 1727-1730.
    • 1 = H): (a) Turner, J. J.; Sikkema, F. D.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Synlett 2001, 1727-1730.
  • 20
    • 33846457075 scopus 로고    scopus 로고
    • 2 = H, R = Bn) under several Mitsunobu conditions, including those reported in refs 7 and 8.
    • 2 = H, R = Bn) under several Mitsunobu conditions, including those reported in refs 7 and 8.
  • 21
    • 33846403428 scopus 로고    scopus 로고
    • Alternative access to β-N-peptidyl-azaserinates 9 was also explored from α-amino esters (including unhindered benzyl glycinate) and α-substituted serines with the hydroxy group activated as O-mesylate 13 and lactone 14, but all attempts to prepare the desired α,β-diamino esters met with failure. (Chemical Equation Presented)
    • Alternative access to β-N-peptidyl-azaserinates 9 was also explored from α-amino esters (including unhindered benzyl glycinate) and α-substituted serines with the hydroxy group activated as O-mesylate 13 and lactone 14, but all attempts to prepare the desired α,β-diamino esters met with failure. (Chemical Equation Presented)
  • 22
    • 33748605775 scopus 로고
    • Monographs on the reactivity of aziridines: (a) Tanner, D
    • Monographs on the reactivity of aziridines: (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
    • (1994) Angew. Chem., Int. Ed. Engl , vol.33 , pp. 599-619
  • 26
    • 84987557280 scopus 로고    scopus 로고
    • Available from (D)-serine. See: Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194-1216.
    • Available from (D)-serine. See: Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194-1216.
  • 27
    • 3342925158 scopus 로고    scopus 로고
    • For a related one-pot tosylation/aziridination of α,β- aminoalcohols, see
    • For a related one-pot tosylation/aziridination of α,β- aminoalcohols, see: Bieber, L. W.; de Araujo, M. C. F. Molecules 2002, 7, 902-906.
    • (2002) Molecules , vol.7 , pp. 902-906
    • Bieber, L.W.1    de Araujo, M.C.F.2
  • 28
    • 17844401298 scopus 로고    scopus 로고
    • To the best of our knowledge, these examples represent the first general preparation of α-substituted β-N-peptidyl-azaserines in enantiopure form. For stereocontrolled synthesis of α-substituted β-N-alkyl-azaserines, see: (a) Pfammatter, E.; Seebach, D. Liebigs Ann. Chem. 1991, 1323-1336.
    • To the best of our knowledge, these examples represent the first general preparation of α-substituted β-N-peptidyl-azaserines in enantiopure form. For stereocontrolled synthesis of α-substituted β-N-alkyl-azaserines, see: (a) Pfammatter, E.; Seebach, D. Liebigs Ann. Chem. 1991, 1323-1336.
  • 30
    • 33846450743 scopus 로고    scopus 로고
    • For a related carboxylic acid-amine cyclization on α-unsubstituted β-N-peptidyl azaserines, see ref 6a
    • For a related carboxylic acid-amine cyclization on α-unsubstituted β-N-peptidyl azaserines, see ref 6a.
  • 31
    • 33846437166 scopus 로고
    • A survey of procedures to obtain 2-azetidinones by cyclization of β-amino esters:, Müller, E, Bayer, O, Eds, Thieme: Stuttgart
    • A survey of procedures to obtain 2-azetidinones by cyclization of β-amino esters: Backes, J. In Houben-Weyl, Methoden der Organischen Chemie, Band E16b: Müller, E., Bayer, O., Eds.; Thieme: Stuttgart, 1991; pp 97-101.
    • (1991) Houben-Weyl, Methoden der Organischen Chemie, Band E16b , pp. 97-101
    • Backes, J.1
  • 32
    • 33846449975 scopus 로고    scopus 로고
    • β-Aminoalcohol tert-butyldimethylsilyl ethers 26 were prepared in 75-95% overall yields from the corresponding α-amino acids. See Supporting Information for details.
    • β-Aminoalcohol tert-butyldimethylsilyl ethers 26 were prepared in 75-95% overall yields from the corresponding α-amino acids. See Supporting Information for details.
  • 35
    • 30044437894 scopus 로고    scopus 로고
    • For some reviews on the preparation of α,α-disubstituted amino esters, see: a
    • For some reviews on the preparation of α,α-disubstituted amino esters, see: (a) Ohfune, Y.; Shinada, T. Eur. J. Org. Chem. 2005, 5127-5143.
    • (2005) Eur. J. Org. Chem , pp. 5127-5143
    • Ohfune, Y.1    Shinada, T.2
  • 39
    • 33846408753 scopus 로고    scopus 로고
    • 3N (water-soluble carbodiimide method), complete epimerization was observed at the α′ position.
    • 3N ("water-soluble carbodiimide method"), complete epimerization was observed at the α′ position.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.