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Volumn 69, Issue 26, 2004, Pages 9100-9108

Dimerization of butenolide structures. A biomimetic approach to the dimeric sesquiterpene lactones (±)-biatractylolide and (±)- biepiasterolide

Author keywords

[No Author keywords available]

Indexed keywords

BIOMIMETIC MATERIALS; BIOSYNTHESIS; DIMERIZATION; FREE RADICALS; KETONES; MOLECULAR STRUCTURE;

EID: 10844221643     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0488053     Document Type: Article
Times cited : (63)

References (38)
  • 5
    • 0033030681 scopus 로고    scopus 로고
    • Huang, Z.; Lin, Y.; Liu, S.; Chan, W. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1999, 38B, 106. Note: In this article, the absolute stereochemistry at the C5 (C5a) center of the trans-C5 (C5a)-C10 (C10a) fused decalin ring system appears incorrectly assigned (according to the CIP system nomenclature) and should be 5R (5aR).
    • (1999) Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. , vol.38 B , pp. 106
    • Huang, Z.1    Lin, Y.2    Liu, S.3    Chan, W.4
  • 11
    • 10844269676 scopus 로고    scopus 로고
    • note
    • For example, a pinacol-type dimerization of a keto form of 4 followed by bislactonization.
  • 20
    • 10844278260 scopus 로고    scopus 로고
    • note
    • The diastereomeric ratio was determined by NMR analysis conducted after a two-phase workup and careful purification by flash chromatography.
  • 32
    • 10844273259 scopus 로고    scopus 로고
    • note
    • The atomic coordinates for 4 (deposition number CCDC 235995), 1 (deposition number CCDC 207880), 2 (deposition number CCDC 207879), and 29 (deposition number CCDC 254587) are available upon request from the Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, U.K. The crystallographic numbering system differs from that used in the test; therefore, any request should be accompanied by the full literature citation of this paper.
  • 33
    • 10844250196 scopus 로고    scopus 로고
    • note
    • The dimer diastereomeric ratios were determined after careful purification by flash chromatography and preparative TLC by NMR analysis. Likewise, the diastereomeric ratio of butenolide 30 was determined by NMR analysis after purification.
  • 34
    • 10844234848 scopus 로고    scopus 로고
    • note
    • Yields quoted are based upon recovered hydroxyatractylolide 4.
  • 35
    • 10844222816 scopus 로고    scopus 로고
    • note
    • Yields quoted are based upon recovered atractylon 7.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.