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Volumn 62, Issue 22, 1997, Pages 7544-7545

First total synthesis of acerogenin C and aceroside IV

Author keywords

[No Author keywords available]

Indexed keywords

ACEROGENIN C; ACEROSIDE IV; HERBACEOUS AGENT; UNCLASSIFIED DRUG;

EID: 0030773677     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9714324     Document Type: Article
Times cited : (39)

References (33)
  • 8
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    • The Chemistry of Natural Diarylheptanoids
    • Atta-ur-Rahman, Ed.; Elsevier Science B.V.: New York
    • Keserü, G. M.; Nogradi, M. The Chemistry of Natural Diarylheptanoids. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science B.V.: New York, 1995; Vol. 17, pp 357-394.
    • (1995) Studies in Natural Products Chemistry , vol.17 , pp. 357-394
    • Keserü, G.M.1    Nogradi, M.2
  • 9
    • 37049108166 scopus 로고
    • The oxidative coupling of phenol promoted by thallium tris-(trifluoroacetate) has been reported to give macrocyclic diaryl ethers; see: Whiting, D. A.; Wood, A. F. J. Chem. Soc., Perkin Trans. 1 1980, 623-628.
    • (1980) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 623-628
    • Whiting, D.A.1    Wood, A.F.2
  • 13
    • 1542527790 scopus 로고    scopus 로고
    • (a) Zhu, J. Synlett 1997, 133-144.
    • (1997) Synlett , pp. 133-144
    • Zhu, J.1
  • 25
    • 9844227786 scopus 로고    scopus 로고
    • A mixture of cyclic and noncyclic dimers was also isolated, which accounts for the total mass balance of the reaction
    • A mixture of cyclic and noncyclic dimers was also isolated, which accounts for the total mass balance of the reaction.
  • 27
    • 3042988525 scopus 로고
    • Molecular modeling [MM2 (Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127-8134), water set)] of compound 3 showed that the lowest energy conformation was indeed the folded one. Similar computational studies have been carried out by Abramovitch's group; see ref 11.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 8127-8134
    • Allinger, N.L.1
  • 28
    • 9844219622 scopus 로고    scopus 로고
    • note
    • -4 M, MeCN). However, further studies are required before drawing any conclusion. Detailed NMR studies are in progress.
  • 29
    • 9844269483 scopus 로고    scopus 로고
    • note
    • As suggested by one of the reviewers, it would be interesting check the outcome of an alternative synthetic strategy, i.e., formation of the biaryl ether followed by macrocyclization via intramolecular alkylation of the keto ester. The cyclization results will provide a direct evidence of our hypothesis as intramolecular recognition phenomena will be absent in this case. This study will be incorporated in a future full account.
  • 33
    • 9844228966 scopus 로고    scopus 로고
    • We have been informed that Professor Nogradi has also accomplished, very recently, a total synthesis of acerogenin C
    • We have been informed that Professor Nogradi has also accomplished, very recently, a total synthesis of acerogenin C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.