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Volumn 121, Issue 49, 1999, Pages 11261-11266

Efficient and practical synthesis of a potent anti-MRSA β- methylcarbapenem containing a releasable side chain

Author keywords

[No Author keywords available]

Indexed keywords

BENZENESULFONIC ACID DERIVATIVE; CARBAPENEM DERIVATIVE; NAPHTHALENE DERIVATIVE; TITANIUM DERIVATIVE;

EID: 0033572694     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992486t     Document Type: Article
Times cited : (27)

References (23)
  • 1
    • 0003491440 scopus 로고
    • (Hauben Weyl); Klamann, D., Ed.; Georg Thieme Verlag: Stuttgart, Band E16b
    • Backes, J. In Methoden der Organischen Chemie (Hauben Weyl); Klamann, D., Ed.; Georg Thieme Verlag: Stuttgart, 1991; Band E16b.
    • (1991) Methoden der Organischen Chemie
    • Backes, J.1
  • 7
    • 0000276556 scopus 로고
    • Trost, B. M., Fleming, I., Ed.; Pergamon Press: Oxford
    • For a review of Pd-catalyzed π-allyl coupling, see: Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Ed.; Pergamon Press: Oxford, 1991; Vol. 4, p 585.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 585
    • Godleski, S.A.1
  • 12
    • 0030028910 scopus 로고    scopus 로고
    • For a comprehensive review of the chemistry of 9, see: Berks, A. H. Tetrahedron 1996, 52, 331.
    • (1996) Tetrahedron , vol.52 , pp. 331
    • Berks, A.H.1
  • 15
    • 0343635330 scopus 로고    scopus 로고
    • note
    • (c) We have realized an alternative, much simpler approach from the acid 9 to the hydroxymethyl ketone β-10: activation of 9 using carbonyldiimidazole is followed by reaction with the glycolic acid enolate. Acid workup with concomitant decarboxylation gives β-10 in 72% isolated yield.
  • 20
    • 0343635329 scopus 로고    scopus 로고
    • note
    • Heptane was chosen for its commercial availability; running the reaction in nonane or in heptane under pressure at 120 °C allows completion of the reaction in 3 h.
  • 22
    • 0342765111 scopus 로고    scopus 로고
    • note
    • 3As.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.