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Volumn 4, Issue 17, 2002, Pages 2833-2836

On the verge of axial chirality: Atroposelective synthesis of the AB-biaryl fragment of vancomycin

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; CHLORINE; LACTONE; VANCOMYCIN;

EID: 0038059973     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026182e     Document Type: Article
Times cited : (31)

References (37)
  • 16
    • 84872266869 scopus 로고    scopus 로고
    • note
    • For a very similar synthetic approach, albeit with only low coupling yields and without considering the phenomenon of atropoisomerism, see ref 7a.
  • 22
    • 84872262337 scopus 로고    scopus 로고
    • note
    • In comparison to 10, coupling of the analogous bromoacid proceeded with only 26% yield; see ref 7a.
  • 26
    • 84872263574 scopus 로고    scopus 로고
    • note
    • For elucidation of the configuration of (P)-12 by quantum chemical CD calculations, see Supporting Information.
  • 27
    • 84872273709 scopus 로고    scopus 로고
    • note
    • Structurally closely related and sterically only slightly more hindered but configurationally stable biaryls are described in refs 7e and 7g.
  • 28
    • 84872273041 scopus 로고    scopus 로고
    • note
    • For atropoisomerization of related biaryls, see refs 5a and 5e.
  • 29
    • 0035805364 scopus 로고    scopus 로고
    • For a related oxidative recycling back to a lactone intermediate, see: Bringmann, G.; Menche, D. Angew. Chem., Int. Ed. 2001, 40, 1687-1690.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 1687-1690
    • Bringmann, G.1    Menche, D.2
  • 32
  • 36
    • 84872266547 scopus 로고    scopus 로고
    • note
    • That this 66:34 ratio is not the equilibrium value was shown by heating the mixture further under the same conditions, ultimately leading to a ca. 53:47 ratio; see Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.