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Volumn 118, Issue 41, 1996, Pages 9884-9891

A highly stereoselective and practical total synthesis of the tricyclic β-lactam antibiotic GV104326 (4-methoxytrinem)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE; SANFETRINEM;

EID: 0029961308     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962006n     Document Type: Article
Times cited : (48)

References (64)
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    • For recent reviews on β-lactam antibotics, see: (a) Berko, A. H. Tetrahedron 1996, 52, 331. (b) The Organic Chemistry of β-Lactams; Georg, G I., Ed.; VCH Publications, Inc.: New York, 1993 and references cited therein. (c) Neuhaus, F. C.; Georgopapadakou, N. H. In Emerging Targets in Antibacterial and Antifungal Chemotherapy; Sutcliffe, J., Georgopapadakou, N. H., Eds.; Chapman and Hall: New York, 1992. (d) Georgopapadakou, N. H. Antimicrobial Agents Ann. 1988, 3, 409.
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    • VCH Publications, Inc.: New York, and references cited therein
    • For recent reviews on β-lactam antibotics, see: (a) Berko, A. H. Tetrahedron 1996, 52, 331. (b) The Organic Chemistry of β-Lactams; Georg, G I., Ed.; VCH Publications, Inc.: New York, 1993 and references cited therein. (c) Neuhaus, F. C.; Georgopapadakou, N. H. In Emerging Targets in Antibacterial and Antifungal Chemotherapy; Sutcliffe, J., Georgopapadakou, N. H., Eds.; Chapman and Hall: New York, 1992. (d) Georgopapadakou, N. H. Antimicrobial Agents Ann. 1988, 3, 409.
    • (1993) The Organic Chemistry of β-Lactams
    • Georg, G.I.1
  • 3
    • 0030028910 scopus 로고    scopus 로고
    • Sutcliffe, J., Georgopapadakou, N. H., Eds.; Chapman and Hall: New York
    • For recent reviews on β-lactam antibotics, see: (a) Berko, A. H. Tetrahedron 1996, 52, 331. (b) The Organic Chemistry of β-Lactams; Georg, G I., Ed.; VCH Publications, Inc.: New York, 1993 and references cited therein. (c) Neuhaus, F. C.; Georgopapadakou, N. H. In Emerging Targets in Antibacterial and Antifungal Chemotherapy; Sutcliffe, J., Georgopapadakou, N. H., Eds.; Chapman and Hall: New York, 1992. (d) Georgopapadakou, N. H. Antimicrobial Agents Ann. 1988, 3, 409.
    • (1992) Emerging Targets in Antibacterial and Antifungal Chemotherapy
    • Neuhaus, F.C.1    Georgopapadakou, N.H.2
  • 4
    • 0024247254 scopus 로고
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  • 20
    • 10344249719 scopus 로고    scopus 로고
    • Eur. Pat. Appl. EP 0 466 509
    • (f) Tamburini, B.; Perboni, A.; Rossi, T.; Donati, D.; Andreotti, D.; Gaviraghi, G.; Carlesso, R.; Bismara, C. Eur. Pat. Appl. EP 416 953 (cl. C07D477/00), 13 March 1991. Chem. Abstr. 1992, 116. 235 337t. Perboni, A.; Bismara, C.; Pentassuglia, G. Eur. Pat. Appl. EP 0 466 509.
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    • van der Groot, H., Domany, G., Pallos, L., Timmerman, H., Eds.; Elsevier: Amsterdam
    • (g) Hanessian, S.; Desilets, D. In Trends in Medicinal Chemistry; van der Groot, H., Domany, G., Pallos, L., Timmerman, H., Eds.; Elsevier: Amsterdam, 1989; p 165.
    • (1989) Trends in Medicinal Chemistry , pp. 165
    • Hanessian, S.1    Desilets, D.2
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    • PCT Appl. WO95/26333
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    • Rossi, T.1    Zarantonello, P.2    Thomas, J.R.3
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    • note
    • 4-Acetoxy-3-[(R)-1-((tert-butyldimethylsilyl)oxy)ethyl]-2-azetidinone is commercially available from Kaneka America Corp., New York, NY, or Aldrich Chemical Co., Milwaukee, WI.
  • 54
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    • For an excellent review on the structure and reactivity of lithium enolates, see: Seebach. D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624.
    • (1988) Angew. Chem., Int. Ed. Engl. , vol.27 , pp. 1624
    • Seebach, D.1
  • 62
    • 0000003263 scopus 로고
    • For the use of amidines as bases in salt formation, see: Shibuya, M.; Kuretani, M.; Kubota, S. Tetrahedron 1982, 38, 2659. Heinzer, F.; Soukup, M.; Eschenmoser, A. Helv. Chim. Acta 1978, 61, 2851. See also, refs 7a, 7b, and 10.
    • (1982) Tetrahedron , vol.38 , pp. 2659
    • Shibuya, M.1    Kuretani, M.2    Kubota, S.3
  • 63
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    • See also, refs 7a, 7b, and 10
    • For the use of amidines as bases in salt formation, see: Shibuya, M.; Kuretani, M.; Kubota, S. Tetrahedron 1982, 38, 2659. Heinzer, F.; Soukup, M.; Eschenmoser, A. Helv. Chim. Acta 1978, 61, 2851. See also, refs 7a, 7b, and 10.
    • (1978) Helv. Chim. Acta , vol.61 , pp. 2851
    • Heinzer, F.1    Soukup, M.2    Eschenmoser, A.3


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