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Volumn 125, Issue 43, 2003, Pages 13155-13164

Total Syntheses of Furaquinocin A, B, and E

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION;

EID: 0142213972     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0364118     Document Type: Article
Times cited : (145)

References (61)
  • 26
    • 0036371962 scopus 로고    scopus 로고
    • Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. For a recent review: Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1.
    • (2002) Chem. Pharm. Bull. , vol.50 , pp. 1
    • Trost, B.M.1
  • 33
    • 0142150502 scopus 로고    scopus 로고
    • note
    • The carbonates were obtained from the corresponding Baylis-Hillman adducts in good yields by reaction with methylchloroformate/potassium carbonate.
  • 38
    • 0142243618 scopus 로고    scopus 로고
    • note
    • This diastereomeric ratio reflects the ratio of (R,R)-31 and meso-31. No (S,S)-31 was formed.
  • 42
    • 0142243616 scopus 로고    scopus 로고
    • note
    • Bromination of acetate 32, the free phenol 33, or the corresponding TBDMS-ether were unselective.
  • 44
    • 0033856957 scopus 로고    scopus 로고
    • Cytotoxicity of the compounds was evaluated in HEK293T, LnCAP and A2780 cell lines using viable stainin with Alamar Blue (O'Brien, J.; Wilson, I.; Orton, T.; Pognan, F. Eur. J. Biochem. 2000, 267, 5421.
    • (2000) Eur. J. Biochem. , vol.267 , pp. 5421
    • O'Brien, J.1    Wilson, I.2    Orton, T.3    Pognan, F.4
  • 45
    • 0142150496 scopus 로고    scopus 로고
    • note
    • We believed that we could access the secondary alcohol 53 by palladium-catalyzed reductive opening of the vinyl epoxide 54. Attempts to selectively epoxidize the disubstituted double bond of dienes 43 and 44 failed. An alternative approach toward the epoxide 53 would be the addition of sulfur ylides to the aldehyde 58. Initial attempts in this directions were not successful, and this route was therefore abandoned. (diagram presented)
  • 58
    • 0142150493 scopus 로고    scopus 로고
    • note
    • The free alcohol 53 or the TBDMS-protected derivative led to inferior results in the cross metathesis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.